


Hypothetically Speaking

by chilly83



Category: Chicago PD (TV)
Genre: Ensemble Cast
Language: English
Status: In-Progress
Published: 2020-06-07
Updated: 2020-10-04
Packaged: 2021-03-04 07:22:38
Rating: Not Rated
Warnings: No Archive Warnings Apply
Chapters: 17
Words: 54,527
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24589777
Author URL: https://archiveofourown.org/users/chilly83/pseuds/chilly83
Summary: What if Hailey had turned down Voight's offer to join the Intelligence Unit?  Would they still remain in each other's orbit?A rewrite of season 5 with Hailey and Jay bonding over friendship instead of partnership.This is an Upstead A/U Fic.
Relationships: Jay Halstead & Hailey Upton, Jay Halstead/Hailey Upton
Comments: 67
Kudos: 155





	1. Chapter 1

**Author's Note:**

> Before we jump in, I do want to give a heads up. This first chapter discusses the events of Season 5 Episode 1 when a bullet fired by Jay goes through an offender and kills a little girl, Morgan. I realize this was a hard episode to watch and for that reason, I am giving the heads up in the author’s note so that you can turn away if you want to. This is in absolutely no way meant to be any kind of statement, this is just a rewrite of the original episode. 
> 
> I am in no way an expert on police reform or politics and I would not attempt to convince or influence your beliefs through my fanfiction writing. 
> 
> Once again, I have to say thank you for taking a moment to read. This story will be multichapter and A/U but follow the cases that Intelligence work through season 5 and part of 6. I have been working on this for a few weeks and I am excited to finally share. Unfortunately, I will not be able to update as often as I normally do, so I hope the longer chapters makes up for this. Thanks to the Let’s Talk Upstead group chat on tumblr for the support and thanks to Leigh0723 for doing the beta reading!

Hailey would normally be annoyed that the tv in the Robbery/Homicide bullpen was on. She preferred to do her work with as little background noise as possible. However, the past few days had been but normal. A few days ago, a unit she had worked with made the news due to an officer involved shooting. A little girl, Morgan, sadly had been caught in the crossfire of a gun bust gone wrong and died. She was shocked to hear the officer involved was Jay Halstead. Hailey, as well as the city of Chicago, were glued to the news waiting for updates. 

She had only worked with Jay for a few days, but it was enough to see what kind of cop he was. She quickly realized he was the guy you would want next to you in a high stress situation like a shootout. If she had joined Intelligence, she would have hoped to be partnered with him. 

Hailey wanted to reach out to Jay, but she wasn’t sure he would take her calls. On the one hand, being responsible for the death of a child was devasting and she knew he would need a friend. On the other hand, she was hardly a friend of Jay’s. She was someone that worked a case with Intelligence a couple of weeks ago. 

She could have been a friend, if she had taken the spot that was offered on the team by Voight. But she wasn’t ready, and she knew it. She was aware they did a lot of undercover work, and she had still not recovered from the last undercover operation she did. She still struggled to deal with the emotional trauma the assignment had left her with. 

She couldn’t shake the nerves that thinking about it brought up, and that was enough to make her turn down the offer. How could she expect a team to trust her when she wasn’t sure she could trust herself not to freak out if things went wrong.

Even though she knew he had a team he could lean on, she also knew that he had recently lost his partner to the FBI. She stared at her blank computer screen as she listened to the newscaster in the background discussing the case. She remembered what it was like for herself when she was involved in an officer involved shooting. The looks you get from other cops, the guilt you feel during every waking moment, the nightmares that come nightly. After a little bit of back and forth, she made up her mind and dialed the number to the 21st District. 

“21st this is Sgt. Platt.” The voice that answered the phone stated.

“Sgt. Platt. This is Detective Upton, Robbery/Homicide.” She said a little unsure of if the sergeant would remember her.

“Hailey! What can I do for you?” Trudy asked, excited to hear from the detective again. While initially she had not made the best first impression on the sergeant, Trudy had warmed up to Hailey when she recounted their history together. She gave Hailey her card and told her to call if she ever needed help with anything personal or professional.

“Hey Trudy.” Hailey said relieved. “I was calling” she started before pausing. She kicked herself for not thinking of what to say before she called. “I was hoping to speak to Halstead.” She finally spit out. 

“Halstead?” Trudy asked. 

“Ya. I uh” Hailey could feel her cheeks turning red “I wanted to see how he was doing. I heard about the shooting.” She said as she rubbed her temples. “I just wanted to reach out.”

“He’s not here.” Trudy said as she let out a deep sigh. “He’s been sent home until the investigation is done.” 

“I see.” Hailey said with disappointment. 

“Is this your cell?” Trudy followed up as she fumbled through her own phone.

“Yes, this is my cell phone.” She responded as she heard a shuffling sound on the other end.

“I sent you his number.” Trudy said as Hailey let out a breath of relief.

“Thank you, sergeant. I appreciate it.”

“Hailey?” Trudy said hoping to catch Hailey before she hung up.

“Ya?”

“He needs a friend.” Trudy said as she hung up. 

Hailey nodded to herself as she hung up her end. _He needs a friend_. The sentence resonated with her. Did he not have any? She did not see his unit turning their backs on him. Was there more to the story than she was seeing? Could the loss of his partner be the reason Platt thought he needed a friend? 

Hailey put the phone number into her phone and started typing out a text.

_Hey, this is Hailey…… (Delete, delete, delete)_

Nope. That wouldn’t work. No guarantee he would remember her.

_Hello, this is Detective Upton from robbery……(Delete, delete, delete)_

That sounded like the beginning of an official call.

_Hi Jay. This is Upton. You know, the one that spilled coffee on Platt. (Delete, delete, delete)_

With a deep sigh, she set her phone down and laid her head in her hands. She didn’t know what was bothering her today; why she couldn’t find the words to say I’m here if you need a friend. She picked up the phone and decided no matter what popped up on her screen, she was sending it. She let her fingers take over and without rereading what she wrote, she sent it. She set her phone face down on her desk and went back to work.

Jay was sitting in his truck in the hospital parking lot when he heard his phone ding. He had driven around Chicago for a couple of hours after being sent home by Voight. He was trying to clear his mind, but it wasn’t working. He tried calling Erin, knowing she wouldn’t answer, but hoping maybe this time she would. Ultimately, he ended up at the hospital again, hoping Will would be available for a quick talk. He was just about to get out to look for his brother when he heard his phone. 

He thought for sure it would be Will responding to the earlier text saying he was stopping by. Instead, it was an unknown number with an unexpected message.

_Hey Jay. This is Hailey Upton, we worked the Lavar Spann case together a couple of weeks ago. I was just reaching out to let you know I am sorry about the shooting. I know Intelligence has your back but if there is anything I can do or anything you need; this is my number._

Jay blinked a few times as he reread the text over and over. He remembered Hailey, even though they only worked the one case together. He was surprised to hear from her, but not at all disappointed. He chuckled at the thought he could have forgotten her after the way she kicked Hank out of the initial crime scene. As Jay typed out a response, he realized it was the first time he had smiled since the gun bust went terribly wrong. 

_Thanks Hailey. I appreciate it._

After Jay’s response, Hailey continued to follow the investigation. She checked in with Platt to find to see if they had heard anything. She called Voight to find out if Jay needed character witnesses. She was about to reach out to Jay again when her phone lit up with a new message.

_I’m cleared. Ballistics came back, bullet travelled through offender then went through the door and hit Morgan. Alderman Price invited me to a press conference to announce it._

_That is such a relief Jay. I am happy to hear the news_. Hailey typed after letting a deep sigh of relief.

_Doesn’t change the fact that I am responsible for her death._

Jay was taken back by his text. His guilt had been eating him alive, but he had not shared it with anyone except Will. Had he really revealed that much to someone who was practically a stranger? 

_It could have happened to any cop in that situation Jay. It was a cruel twist of fate that carried the bullet through the door. What are the details for the press conference?_

_3 pm at the community center in Morgan’s neighborhood._

Hailey looked at her clock. It was already 2 and she still had a ton of work to do. 

_I am going to try my hardest to be there._

Jay once again felt a smile grow on his face. It was a small one, but it was the first one he had since the last time he spoke with Hailey. Not even news of the investigation clearing him had been able to make him smile. They proved he did not purposely or recklessly kill Morgan, but he was still the one responsible for her death. It was still a burden he would have to carry. 

Jay wanted to tell Hailey not to worry about it, but truth be told, he could use someone in his corner for the conference. He wasn’t sure what to expect so knowing he had a least one other person there supporting him made him feel better. 

By the time Hailey got to the front of the community center, the press conference had already ended. She looked around at the scattering crowd and spotted a familiar figure. She ran to catch up to Jay not wanting to miss him. 

“Hey!” She yelled as she got closer.

“Hey.” Jay called out as he turned towards her voice. 

“Sorry. I got here as fast as I could. It’s over?” She asked keeping her eyes glued to his face as they walked across the street.

“Yeah, just ended.”

“How’d it go?”

“It was good.” Jay said while letting out a sigh. “Really good actually. Price was very gracious.” He said with a confused look on his face. He stopped in front of his truck and when he turned to see Hailey smiling at the news, he couldn’t help but smile back. “I’m not really sure what prompted all this, but—”

“Hey, take yes for an answer.” Hailey said with a shoulder shrug and smile. 

He wasn’t sure why she was going out of her way to reach out to him, but he appreciated it. They stood there for a few seconds just looking at each other, each one feeling at ease with silence, before Hailey finally broke it. 

“If there is anything you need, please let me know.” She said with a kind smile.

Jay nodded in response and was able to muster a small smile for the detective he hardly knows. 

“I’ll be ok eventually. I think I just gotta make sense of it all.”

“Yeah.” Hailey said as she looked away. “It’s tough. Trust me.” Jay noted the sad smile on Hailey’s face and the way she folded her arms across her chest. He realized then why she had been reaching out.

“Have you…” Jay couldn’t bring himself to finish the question. He didn’t need to; Hailey understood exactly what he was asking.

“Yeah.” She said as she tilted her head and nodded slowly. She didn’t know what prompted her to answer, it was not something she ever talked about and not something she wanted people to know. “Different circumstances, but….” She answered. 

He looked at her and nodded in understanding. He put his hands in his pocket and met her gaze. He noted the relaxed posture and peaceful look on her face. She had clearly been through a tough situation like he had; and seeing her come out of it at peace made him hopeful for his journey ahead. After a few seconds of looking at each other, Hailey once again broke the silence. 

“Talk to Morgan’s mother yet?”

“No.” Jay said with a firm head shake. “I don’t think I am ready.” Hailey noted his tense shoulders and how his eyebrows had been furrowed throughout the whole conversation. She wanted so much for him to be able to move on. 

“You’re never going to be ready.” She said softly. “You just have to do it.”

For the first time that conversation, Hailey saw his smile reach his eyes. She found the smile to be contagious as she felt her face light up seeing it. Jay nodded in understanding. 

“I can go with you. If you think that helps?” She offered.

“Thanks, but I think I need to do this alone.”

“Let me know how it goes. And seriously, if you need anything, even just someone to sit next to you at a bar, please let me know.” She said as she reached out and placed her hand on his arm. 

He smiled at her and she turned to walk away but didn’t get far.

“Hailey?” She heard Jay call. She turned around to see Jay still standing next to his truck.

“Thank you.” He simply said.

“No problem.” She said as she walked away. 


	2. Chapter 2

**Notes for the Chapter:**

> I posted Chapters 1 and 2 together. Please be sure to go back and read Chapter 1 if you missed it! Thank you so much for taking the time to read. Thank you also to my beta reader Leigh0723 for your help!!!!

Jay texted Hailey to let her know he spoke to Morgan’s mom and thanked her for her advice and friendship. It had been weeks since that text and Hailey had not heard from Jay. Crime picked up for both detectives, so the workdays were long and the exhaustion at night was brutal. Antonio returned to Intelligence to fill the vacant spot left by Erin. He had been partnered up with Kim, leaving Al as Jay’s partner.

Jay enjoyed working with Al, he had a calming presence that Jay admired. The years of experience was also a plus for Jay as there wasn’t much Al hadn’t already seen or been through. Unfortunately, Jay was still struggling with his role in Morgan’s death as well as the loss of Erin. 

He found himself sitting alone in his apartment often, drinking and just trying to forget. He often thought about calling Hailey, but he never ended up doing it. He had closed himself off to the world except for Will. Not that he hadn’t tried, Will just would not let him.

One night, Will and Natalie had a babysitter so they could go on a date. When Will spent the whole car ride home from Med plus the 30 minutes getting ready talking about Jay, Natalie decided inviting Jay along would be good for both brothers. Will was grateful for the gesture and text Jay to let him know.

As fate would have it, the group ended up at Bartoli’s, a local restaurant that Natalie swore had the best deep dish in Chicago. Will and Jay weren’t picky, so they went along with her suggestion. They had just been seated when Jay noticed a familiar blonde ponytail walking into the restaurant. 

Will was talking when he noticed that Jay had been distracted by something near the front door. He turned to look and saw the woman that Jay was staring at.

“You know her?” Will asked.

“Yeah, she’s a friend from work.” Jay said as he stood and excused himself. He began walking towards the hostess stand and called out to her.

“Hailey!” He said as he approached. 

“Jay!” She said once she realized who had called her. She smiled at the sight of the detective walking towards her. Her heart fluttered when he returned an equally bright smile at her. Jay was almost to the hostess stand when he heard an older man calling.

“Detective!” The man said causing both Hailey and Jay to stop and turn. Jay was confused as to how this person knew he was an officer until he saw Hailey walking towards him. He continued his route to the hostess stand, intent on speaking to Hailey. 

“How is my favorite detective?” The older man asked as he pulled Hailey in for a hug.

“Good Niko. Just picking up some takeout.” She said with a smile as he released her.

“I told you to call me before you order. Your money is no good here.” The older man chastised the detective. He began walking towards the hostess stand looking through the receipts on the counter. 

“That’s exactly why I didn’t call you!” She laughed as she playfully swatted at his arm. “I want to pay Niko, please.” She said as he found the receipt with her name on it. 

“You don’t pay here Detective.” The man said shaking his finger at her as he walked back towards the kitchen. Hailey sighed as she looked at an amused Jay.

“The restaurant was robbed last year. One of his guys in the kitchen was shot. It matched a string of robberies in the area except his cook was lucky and pulled through. Ever since we solved the case, he insists on giving me free food.” She explained.

Jay nodded in understanding. 

“Natalie raves about this place.” He said with a smile. Hailey’s eyes inadvertently widen at the mention of a woman. “My brother’s girlfriend.” Jay followed up, noting the look on Hailey’s face. Hailey smiled shyly at the new information. She knew Jay had caught the look on her face.

“They have the best deep dish in Chicago. I was coming here before the case and I can’t stop. I try to be sneaky and order without Niko finding out but every now and then he catches me. Insists on comping the meal.” She said with a head tilt and shrug as she tried to explain. 

Just then Niko returned with a bag of food.

“Let me pay Niko.” Hailey said sternly to the man. 

“I insist.” The man said as he handed her the bag.

“Do you have plans tonight?” Jay asked after he noticed it was just 1 small container in the bag.

“Just the best deep dish in Chicago and some tv.” She said with an embarrassed chuckle.

“I’m here with my brother and his girlfriend. You should join us.” Jay offered motioning over the table with Will and Natalie. Hailey looked over and waved at the two people sitting who were looking back at her with big smiles on their faces.

“I already got my food,” She said as she held up her bag.

“Then you’ll have leftovers for tomorrow. Come on.” Jay said as he reached for her bag. Hailey could feel herself blushing, although she did not know why. She handed over her bag and followed Jay back to his table. 

“This is my brother Will and his girlfriend Natalie. Guys, this is Hailey.” Jay said as he introduced everyone.

“You guys are doctors over at Med, right?” Hailey asked as she shook Will’s hand. Will and Natalie nodded in response. “I recognize you from the ER.” 

“I’m sorry. I see so many people and so many cops, it’s hard to keep up.” He said, embarrassed that he didn’t remember her. 

“Don’t worry about it.” She said with a smile as she waved off his concern.

“Are you with Intelligence?” Natalie asked.

“No. I work Robbery/Homicide.” She said as the two raised their eyebrows. “I worked on a case with them a few months back.” Hailey stated suddenly feeling the need to explain how they knew each other. When Jay said a friend from work, they assumed someone he worked with. It was now occurring to them he meant a friend that he met through his work. 

The two women continued to talk as Will looked over to Jay with one eyebrow quirked. He knew his brother was struggling with Erin leaving so he was surprised when Jay brought the attractive detective over. Jay rolls his eyes at his brother and tried

to focus on the conversation.

“Usually if I’m at the ER I am interviewing suspects or victims.” Jay hears Hailey say to Natalie. 

“So, no frequent flyer cards for you guys?” Natalie asks with a chuckle looking over to Jay. He didn’t need to hear the first part of the conversation to understand what they are talking about.

“No. We don’t get shot at as much as those guys do. Most action we see is when someone decides to run, and we give chase.” Hailey answers. 

“I keep telling this guy to find something that requires less dodging of bullets.” Will says as he motions towards Jay with his head.

“Apparently lead is bad for you.” Jay says as he tilts his head and whispers to Hailey as if he was telling her the secret to life. His eyes widen at the laugh that erupts from Hailey. It was unexpected and Jay was pleased with himself for making it possible.

“Lead. Fists. Knives. All of it Jay.” Will responds to Jay. 

“If you are going down in a hail of bullets, might well go down as a hero.” Hailey said before she realized how harsh it sounded. “Sorry.” She said as she looked at the surprised faces around the table. “I see tragedy in everything. Side effect of growing up in Greek town.” 

“To Heroes.” Natalie said as she raised her glass. The other three at the table followed suit.

“Plus, being such an elite unit, you get noticed by feds like Lindsey did.” Hailey says as she sets down her glass. She notices how the rest of the table tensed at her comment and she looked to Jay.

Hailey looked around at the faces trying to figure out what she had said wrong. For the second time in just one minute she had managed to put her foot in her mouth.

“I’m sorry. I didn’t mean to upset anyone.” Hailey said with confusion and concern.

“No.” Jay said trying to wave off Hailey’s concern. “It’s all good.” He continued as Will and Natalie laughed off the comment and tried to smile. “The move happened unexpectedly so we are all still trying to wrap our heads around it.” Jay followed up as he took several long gulps of his beer. Natalie smiled softly at Hailey as she noticed Hailey’s demeanor suddenly tense. It was clear to her that Hailey had no idea that Erin and Jay were more than partners. 

When the waiter came around to take their orders the table was relieved for the distraction. Will and Natalie order a pizza to split between the two of them while Jay and Hailey did the same. 

“I have to warn you,” Hailey said leaning in towards Jay “this pizza is going to ruin you for all other pizza.” She said in a matter of fact manner.

“That’s what everyone says about their favorite pizza spot.” Jay said with a chuckle. 

“You’ve been warned.” Hailey said as she held up a finger to Jay in a playfully. Jay shot back a cheeky grin and held his hands up to feign surrender. Will couldn’t help but grin at the interaction he witnessed. He hadn’t seen Jay smile like that in a long time. Even before Erin left, Will had seen the ghosts that haunted Jay’s eyes. Those ghosts lived there now, but somehow Hailey had managed to scare them away momentarily. 

When the pizza finally arrived, Hailey and Natalie could not contain their excitement. 

“You guys are really building this up.” Jay said as the waiter set down the pizzas on the metal stand. “I hope it can live up to the hype.” He said as he reached for a plate.

“WAIT!” Hailey said excitedly. She took the plate from him and moved the pizza closer to her. She grabbed the knife and began to cut a slice as the table watched her confused. 

“To get the real experience, you have to cut it just right,” she said as she slide the pie server under the pizza “so that when you pull it out” she continued as she lifted the slice “you can see the gooey trail the cheese leaves behind!” Jay laughed as she raised the slice over the plate, watching as she tried to scrape all the cheese still attached to the pizza onto his plate. 

“You eat with your eyes before your mouth.” She said as she placed the plate in front of Jay and quirked her eyebrows in excitement. Jay marveled at the smile on her face and momentarily forgot that this was someone he barely knew. The comfort he felt in her presence felt like one you would expect from a lifelong friendship, not one that began a few months earlier. 

Will and Natalie laughed as they watched Jay cut into his pizza. Hailey sat, watching for the moment when Jay finally ate the pizza. The second she saw his eyes widen in surprise, she looked to Natalie and nodded smugly. Natalie quirked an eyebrow in response, knowing they had converted another fan.

“Wow.” Jay said as he chewed and looked to Hailey.

“I told you!” Hailey said with a pleased grin. “Best pizza in Chicago.” She said as she cut herself a slice and began eating. 

“I see why you can’t stop eating here.” Jay responded as he continued to eat. 

The four of them enjoyed their pizza and each other’s company for quite some time. It wasn’t until Natalie’s phone dinged that they realized how long they had been there.

“Oh shoot.” She said as she typed a message into her phone. “It’s already 8, we have to get home to the sitter.” She said as she looked to Will. Will nodded in understanding and waved the waiter over to ask for the check. 

“Mr. Bartoli wanted me to let you guys know dinner is on the house tonight.” He said as he smiled at Hailey. Will and Natalie were floored at the generosity while Jay laughed at Hailey’s irritation. 

“Please tell him thank you.” Hailey said as she shook her head at Jay.

“Do we want to know?” Will asked, witnessing the exchange but not quite understanding it.

“Hailey eats here for free. Apparently, so do her guests.” Jay said with a chuckle. 

“I try not to but the owner refuses to charge me and I can’t find another pizza place that’s half as good.” Hailey said as she shook her head. “I like to leave really big tips to make up for it.” She always felt bad about the free food.

“Sounds good to me.” Will said as he reached for his wallet to pull cash out.

“How often do you eat here?” Natalie asked, curious about Hailey’s arrangement.

“I try to keep it to once every other month.” She said with a chuckle. “Sometimes I can get people to order for me and I am able to get in and out without being seen. But every now and then, Niko recognizes my order and is waiting for me.” Hailey explained. “I think the waiters tip him off.” She said with a laugh. 

“If you are leaving big tips, they are probably really happy to see you!” Will reasoned. 

Just as the four were beginning to stand up, Niko came out with a homemade cheesecake.

“Before you leave, please enjoy some dessert.” He said as he set the cake down. 

“Niko.” Hailey said as she walked over to hug the owner. “Seriously, this is too much.” 

Will and Natalie were overcome with gratitude as they shook the man’s hands and thanked him for the kindness.

“We have to get home to our sitter but thank you so much. It was delicious as always.” Natalie said.

“I will pack it up for you then!” Niko said as he turned to go back to the kitchen for a box. 

“Don’t feel like you two need to rush off.” Will said motioning to Jay and Hailey. “Stay and enjoy the cake!” 

“I rode with you.” Jay said as he put his hands in his pocket, feeling conflicted about what to do. He didn’t want to leave, but he didn’t want to ask Hailey for a ride either.

“I can take you home. The cheesecake is worth it!” She said in response to his statement.

“There you go.” Will said as he stared at Jay hoping he would take the offer. 

Jay looked at Hailey, nodding in acceptance. Will and Natalie smiled in relief, not because they didn’t want Jay’s company. They just hadn’t seen him so happy in such a long time; they didn’t want it to end. Hailey also happened to be a huge fan of Bartoli’s cheesecake, so she used it as an excuse to keep the night going.

Niko returned with a box and put a few slices into it. Natalie and Will thanked him again for his generosity and said good night to Jay and Hailey. 

The two detectives smiled at each other as Jay cut a couple of slices of the cheesecake for them.

“I am sorry if I made you uncomfortable.” She said. “When I brought up Lindsey.” she explained when she saw the confusion on jay’s face.

Jay waved off her concern when he realized what she was talking about. He tried to shake off the apology but realized that Hailey probably didn’t understand what had happened. “We were dating.” Jay said as he looked down at his cheesecake. Hailey’s eyes darted over to Jay at his revelation. “I guess we were technically on a break when she left. I didn’t find out about the job until she was gone.” He said sadly, still looking at his cheesecake. 

Hailey sat frozen. She wasn’t sure what to say or do in response. She never would have guessed that they were involved. She had so many questions, none of which were appropriate to ask. She couldn’t understand how someone could accept a job that required them leaving the state and not tell their partner about it-even if the partner was technically their ex. 

“Jay, I am really sorry.” She said with a soft voice. 

“No worries.” He said hoping to move on from the conversation. “I’m partnered with Olinksy now.” 

Hailey’s eyes widen with her smile as she nodded at Jay.

“That’s good times!” She said genuinely. Al had made an impression on her during the case and she was aware of his all the work he had done on the force.

“He’s good police.” Jay said with a chuckle, remembering the conversation between Al and Hailey while they were doing surveillance. “He’s a bit of a silent genius. Doesn’t talk much but when he does, its prophetic”

“That’s exactly the impression he gave me.” Hailey said with a cheeky grin. 

Hailey wanted to ask Jay how he was doing but she couldn’t bring herself to bring down his mood. He seemed to be enjoying himself and she did not want to be the one to get in the way of that. As she thought back to her nerves about reaching out to him, she realized that she never told him how she got his number.

"I got your number from Platt, by the way. I called the district looking for you and she passed it along." Hailey explained.

"Let me guess. You asked her to take a message and this was easier for her." Jay chuckled. It was no secret Platt despised taking messages.

"So, this happens often?" Hailey asked relieved Jay didn't find it weird that she had his number.

"Not to just anyone but she knows you." He said as he took a sip of his coffee.

"I was worried you guys wouldn't remember me. Figured Platt-" Hailey was cut off by the sound of chuckles coming from Jay. She looked up at him to see him covering his mouth trying not to laugh. When he noticed the confused look on her face, he laughed even more.

"You made such a great first impression. First at the bank when you squared up with Voight, then knocking Platt’s coffee out of her hands. No way we were forgetting you." He said with a playful smile. He was relieved when Hailey laughed in response.

"Maybe it would've been better if you guys forgot." She said playfully as she picked at her cheesecake.

"That actually wasn't my first time meeting Platt." Hailey said. Jay shook his head at the new information.

"Not surprising. Everyone in the department has crossed paths with her at some point."

"Actually, I met her when I was a kid." Hailey replied. She noted how Jay's eyebrows raised in surprise at her revelation. “My dad’s restaurant was robbed when I was working there. She was the responding detective.” She stated in a matter of fact manner.

“I can’t believe you remembered her.” Jay said as he shook his head in disbelief.

“She’s not really the kind of person you forget.” Hailey said with a chuckle.

She didn’t go into detail about how that night changed her life. How something broke in her father during the robbery and it would never be fixed. How shocked she was when she got in her dad's truck after he was released from the hospital and he yelled at her for giving away the money. How he started drinking when they got home and never seemed to stop. How she clung to the memory of sitting at Trudy’s desk and the last time in her childhood she felt safe.

“Did you tell Trudy?"

"Ya." Hailey responded sheepishly. "After I realized who she was. Which unfortunately was after the incident with the coffee." She said with a chuckle. This earned her another laugh from Jay.

"The secondhand embarrassment was strong that day." He said with a cheeky grin. He found it easy to talk to Hailey and began to wonder what it would have been like to have her in the unit.

“Why’d you turn down Intelligence? Voight never told us; just said you declined the offer.” Jay asked curiously. They all thought she would jump at the opportunity to join, and truthfully, they all had hoped she would.

Hailey’s eyes shot down to the table as she let out a soft chuckle. She didn’t know how to explain her decision without actually explaining her decision.

“Voight said they needed a fill in for an officer on leave. I still had open cases to clear and I didn’t want to leave them collecting dust until I got back.” She said with a shrug. Jay nodded slowly, not sure if he believed her but not wanting to call her out on it.

After an hour of talking and slowly eating cheesecake, Hailey began to feel the day catch up with her. She tried not to yawn but found it impossible to keep at bay. 

“We should get going.” Jay said looking at his watch. “We’ve been here for hours!” He said surprised at the time. Hailey looked at her phone and was shocked to see it was already past 9.

“Ya. I have a long day tomorrow. I should really call it a night.” She said as she stood to stretch. When she made eye contact with their waiter, she waved to him to let him know they were leaving. The waiter nodded and ducked into the kitchen before returning with the owner.

“Thank you so much for the meal.” Jay said as he shook Niko’s hand.

“Anything for my favorite detective.” Niko said as he winked at Hailey.

“Careful” Hailey said as she leaned in for a hug, “he’s a detective too. You’re going to hurt his feelings.” 

“Really?” Niko asked as Jay chuckled and nodded. “Next time you come back, make sure you ask for me! I’ll be sure to take care of you.” The owner said as he shook Jay’s hand once again.

“That is not necessary.” Jay said trying to wave off the offer.

“I insist.” The old man replied. “Your money” he said pointing at Jay then back at Hailey “and your money is not good here.” He wished them goodnight as he walked back into the kitchen. 

“Not so funny now is it?” Hailey cheekily asked Jay as they walked out of the restaurant. Jay realized while he was laughing that it had been a long time since he felt that ache in his abs that came along with a good belly laugh. 

The ride to his apartment was quick and uneventful. They carried on a light conversation about the Blackhawks and Jay was surprised to hear Hailey was a big fan. When they arrived at his apartment, Jay found himself sad that the night was ending.

“Thanks for the ride. And dinner.” He said holding up his leftovers.

“No problem Jay. I had a good time.” She said with smile.

“Me too.” Jay said as he opened the car door. He started to get out but suddenly sat back down and shut the door. He scratched his head as he looked at Hailey a bit confused. He wanted to ask her to come upstairs; he didn’t want the night to end but wasn’t sure why. A big part of him just enjoyed Hailey’s company, but another part was curious about what would happen if he invited her upstairs.

“You good?” Hailey asked, pulling Jay out of his thoughts.

Jay turned to answer but couldn’t find the words. He sighed and shook his head hoping the action would get his brain working again. He wanted a distraction; he didn’t want to use Hailey to get it. He had enjoyed her company as a friend, and he didn’t want to assume she wanted any more than that.

“I am really sorry I never called.” He finally said, eyebrows furrowing as he looked her in the eyes. “I meant to. I just.” He shrugged his shoulders, unsure of how to finish the sentence. 

“The offer still stands Jay. If you need someone to talk to, give me a call. If you don’t, then don’t worry about it.” She said as she let out a deep breath. “What happened, it’s not something you can just get over. It takes time. _Work_.” She said emphasizing the last word. “For me, the work I needed to do was with a therapist. For some, the work can be done by talking to someone who understands what you are going through.” She said softly. She paused letting her words sink in, worried that she may have crossed a line. 

When Jay nodded in understanding, she placed a hand on his arm.

“I had a great time.” She said once again. “We could do it again sometime. Or we can wait until I have to escort Intelligence off another crime scene.” She said as Jay laughed. “I am good with either.”

“I will keep all of that in mind.” Jay said as he got out of the car. Before shutting the door, he leaned in one more time. “You could call too you know.” He said with a cheeky grin. 

“I’ll keep that in mind.” Hailey said as she tilted her head and smiled back at Jay.

“Good night Detective.” Jay said with one final smile.

“Good night Detective.” Hailey replied as Jay shut the door. 

**Notes for the Chapter:**

> Sadly the next update will take about a week! Thanks for reading!


	3. Chapter 3

**Notes for the Chapter:**

> Thank you so much for reading and for the reviews! I love reading what you guys have to say. Thanks again to my beta reader Leigh0723 for helping me figure out Hailey’s backstory and the timeline! There is so little known about her, it was hard to piece together her life.

For Hailey, one of the unexpected benefits of working a case with Intelligence was reconnecting with Trudy Platt. When Hailey realized that the desk sergeant she had spilled coffee on was the same detective that had helped her family after the robbery, she made establishing a relationship with Trudy a priority. Hailey knew Trudy had a stellar reputation in the police department. She had found out the hard way that it was harder for women on the force to be taken seriously. If Trudy could offer up any life lessons on how to manage the job without sacrificing who she is, Hailey was ready to listen.

Trudy had asked Hailey to volunteer with her on Saturdays at Community Play, a local organization that ran programs sponsored by Chicago PD to keep kids off the streets. Trudy had been working with teens on setting up a community garden to give families in the neighborhood healthy food options and learn a life skill. She had secured a location and was still working on clearing it out when Hailey offered to help. 

That is how Hailey spent the next 4 Saturdays. She met Trudy and the teens at 8 am at the work site and helped clear debris until 4. A local diner would box lunches up and deliver them to the crew at lunch time, allowing everyone to enjoy a well-deserved break. Hailey would answer questions the teens had about any topic they brought up. She did not shy away from tough conversations and enjoyed her new role as a mentor for the youths.

Hailey was proud of the work she was doing with Community Play. So, when Trudy asked her to take her place at a fundraiser for the event, she was happy to say yes. Sure, it was last minute, and she would have to wear her police uniform, but Hailey didn't have anything else to do. 

She was able to get ready quickly and made it to the banquet hall just after the fundraiser had begun. Trudy told her the table number she was sitting at, so when Hailey walked into the room, she did a quick scan to find the right table. She did not get very far into the banquet hall when she felt a tug at her arm.

“Officer Upton.” A man said as Hailey turned around. She felt herself tense instantly when she realized it was Sgt. McGrady.

“It’s Detective now.” Hailey said curtly as she gently pulled her arm away. 

“Detective.” The man said taking a sip of his drink. “I think I remember hearing something about that.” He said with a grin. “I didn’t realize you were involved with Community Play.” The Sgt said as he took a step towards Hailey. Hailey instinctively took a step back, falling back into the dance she used to do with McGrady. Having worked together previously on a joint operation, Hailey knew McGrady had a habit of standing a little too close to the female officers. She had learned to anticipate when a step forward would be taken so she could take one back casually. 

“I actually just started a month ago. I’m helping Sgt Platt out with one of her projects.” She said with a tight smile. Hailey’s eyes began to search the crowd looking for someone she knew. She wanted to get out of the current conversation without letting McGrady know he made her uncomfortable.

Jay had arrived early to the fundraiser with some other intelligence officers. He went to the bar to grab a soda and was walking back to his table when he noticed a familiar figure. He instantly felt his face light up when he saw Hailey scanning the room. He was surprised, and delighted, to see her. 

He watched as a tall man walked up behind her and tugged on her arm. He noticed the way Hailey nudged her arm free from his grasp and how her body posture changed. He watched her stiffen as her shoulders tense when she began to speak to the man. Jay started to move towards the pair then stopped himself.

He didn’t know a lot about Hailey, and certainly didn’t know what was happening in front of him. For all he knew, this could be a coworker or friend that she is upset with. He watched the man take a step towards her followed immediately by her taking a step back. When he saw her eyes beginning to scan the room once again, he knew she was looking for help.

“Hailey!” He called as he began to walk towards her. He watched as she looked around momentarily before spotting him. He noticed her shoulders instantly relax and chest move as she took in a deep breath. The smile that washed over her face was one that made him forget what he was doing. 

“I should get back to Anne.” McGrady said as he saw Jay approaching. He took a step back from Hailey then reached an arm out to gently touch her shoulder then walked away. 

  
As Jay approached her, Hailey took a deep breath to try to compose herself. She felt the strain in her cheeks from smiling so wide and wondered when the last time anyone had managed to do that to her. When Jay smiled back at her, Hailey had to look away to stop herself from staring. She looked down to the floor then back up at Jay with a shy smile and the slightest head tilt. 

“Hi, Jay.” She said softly when he was finally standing in front of her. She noticed how surprised and happy he seemed to be at seeing her. “Trudy didn’t tell me Intelligence would be here.” She said as she tried to steady her nerves. 

“She invited us.” He said, eyebrows furrowed with confusion. “Price is recognizing the officers that have been running programs with Community Play as a thank you for all their work.” Jay said as Hailey chuckled and shook her head.

“She did not mention that when she asked me to fill in for her last minute.” Hailey said with a laugh. “Does that mean you’re at table 11?” Hailey said hopefully as Jay nodded to her. 

“Come on. There’s a bunch of us here already.” Jay said as he led the way. 

When they arrived, Kevin, Adam and Hank all stood up to greet her. She shook all their hands as they expressed their surprise to see her joining them. When she explained that Platt had asked her to fill in last minute, they all laughed as well. 

“Don’t feel bad. We’ve all been roped in to covering for Platt last minute.” Adam said as he reached out and pat Hailey on the back. 

“The key is to ask a lot of questions.” Kevin followed up. “If you ask enough questions, she’ll drop it.” He said as he raised his glass then paused. “Or go look for Burgess.” He added as an afterthought. 

Hailey laughs and thanks them for the advice. She joins the men at the table and finds herself once again wishing she had joined the unit. The room quiets as Ray Price takes his place at the podium to begin the night. He starts with a speech explaining what Community Play is and how they are making a difference in lives of at-risk youth in the neighborhood. After showing a slide show of photos from different activities, he begins to recognize some of the officers that run programs. Hailey was relieved when she realized that he was not calling them up to the podium, but simply having the room acknowledge them with a round of applause. 

After the speech, the table enjoyed a delicious dinner and each other’s company. Once the tables were cleared, the people at table 11 scattered to mingle with the other officers in attendance. Hailey made her way to the bar and looked down at her watch. She had to kill 15 more minutes on the clock and then she would be free to officially enjoy herself. She watched as Hank made his way over to McGrady and his wife who were seated a few tables back. 

Seeing his wife, Anne, on his arm, laughing along with whatever he had just said made her blood boil. She had gotten to know the woman when she worked in narcotics with the Sgt. Hailey felt bad for her former friend. Trapped in what she thought was a loving marriage, not knowing about her husband's many vices which ran the gamut from gambling to adultery. 

Hailey was pulled from her thoughts when she felt someone sit next to her. She turned to see Jay had made his way to the bar and had sat down next to her. She noticed that he had brought both their jackets with him, setting them down on the seat next to him. 

He let out a deep sigh and put his elbow on the counter, resting his head in his hand. He look over to an amused Hailey and couldn’t help but smile. 

"Do you wanna get out of here?" He asks casually. He isn't expecting the scoff that comes from Hailey's direction.

"Maybe in 30 minutes. Unless you know somewhere else serving free Chantal de Laroque. I'm off in 10 minutes and would love a glass." She says with a coy smile.

"Wow." Jay said as he looked over to Hailey. “You’re really….um, what’s the word. Le snob.” Jay responds with a head tilt and cheeky smirk that caught Hailey off guard. She looks away to hide her blush.

“That’s the Lake Forest in me escaping.” She says with a chuckle.

“What?” Jay says with a dry laugh. “I thought you were from Greek town?” He asks confused. 

“That’s just a story I tell.” Hailey joked as she shook her head and wrinkled her nose. Jay responds with a suspicious nod and smirk.

“I’m just kidding.” Hailey said with a laugh. “We moved there when I was 11.” She further explained.

While they sat at the bar, Hailey couldn’t help feeling like she was being watched. She glanced over her shoulder to see that McGrady was, in fact, watching her from his table. Hailey once again felt her body tense and turned toward the bar, hoping to forget McGrady was there.

Jay noticed Hailey’s body language and turned to see what she had looked at. He felt a slight sting of irritation as he realized the same man he saw her speak to earlier was staring at them. When Jay made eye contact with the man, he quickly averted his gaze away from the bar and toward the woman he was sitting with. 

“You know that guy?” Jay asked. He was done with the guessing game and wanted to know what had made Hailey uncomfortable. He motioned toward the table that McGrady and his wife were sitting at.

Hailey looked in the direction and realized who Jay was talking about.

“Ya, Sean McGrady. Sarge up in narcotics.” She said as she took a long drink of her water. “Couple of years back I was assigned to his joint investigation. Good police.” She says matter of fact without a hint of emotion in her voice. 

“She says with hesitation.” Jay said with raised eyebrows and sarcasm in his tone.

“No. It’s just.” She paused to think of the best way to explain. “He’s competitive. Always looking for an angle. Drove me nuts.” Hailey said as Jay nodded along. He looked at her with a quirked eyebrow that let her know he was waiting for more. “We have a different way of reading things.” She said as she looked off into the distance. Jay’s instincts told him there was more to the story, but he could see how uncomfortable Hailey was.

“You don’t have to wait for me. I can meet you guys later.” She said not wanting to keep Jay from his unit. Jay simply shook his head and looked at his watch. He smiled at Hailey and waved down the bartender. Hailey laughed as he ordered a glass of Chantal de Laroque.

“You are officially off.” He said as he slid the glass towards her. 

“I am going to run to the restroom before I enjoy this treat.” She said as she stood up and excused herself. The more time she spent with Jay the more she kicked herself for turning down Intelligence.

As Hailey left the bathroom, she noticed McGrady and a man she did not recognize arguing. She had every intention of walking right by, until she saw McGrady push the man. 

She ran over calling out for them to stop. 

"What's going on?" She said as she closed in on the men. 

"Nothing." McGrady said, straightening out his uniform and waving Hailey off. "Right?" He said as he looked to the man he was arguing with. 

"Ya." The man said as he turned and walked away. 

"It was good to see you Hailey." McGrady said as he scanned Hailey one more time before he turned to walk away. 

"Wait." She said as she tried to get his attention. He stopped and ran a hand over his face as he turned to face her. Hailey could see that he was irritated but she had no plans to back down. 

"What the hell was that? You're picking fights with people at fundraisers?" She snapped. She watched his expression turn from annoyed to angry as he took a step towards her. Just then, she heard Jay’s voice call her. She turned in time to see Jay run towards her with their jackets in his hand.

Hailey stepped towards Jay as McGrady took a couple of steps back. Jay had his eyes on the Sgt, unsure of what he had interrupted. His eyes snapped to Hailey when he heard her call his name. 

"Jay?" Hailey asked. Jay looked at her then back at the Sgt once more before turning his attention back to Hailey. 

"I gotta go." He said as she grabbed her jacket. "Got shots fired nearby. Active shooter." He said as he began to run off. Hailey turned behind him and took off with him. 

"I'm coming with." She said as she caught up to him and instinctively followed him to his truck. 

The ride to the location of the shots was quick. Hailey barely had enough time to notify her Sgt that she was joining Intelligence to respond to the call. When they arrived, they were met by Kevin, Adam and Hank who all had just arrived. Hailey fell in line with the unit as they entered the house and began to clear it. 

“I’ve got two down!” Hank said as he entered the living room. He rushed over to the bodies lying on the floor and checked their pulses.

“They’re both gone.” He said as he motioned for the officers to continue clearing the house. Jay and Hailey had already made their way upstairs and found another body in the first room they checked. Jay scanned the room as he entered, Hailey behind him to cover his back. Jay approached the man and reached for a pulse. 

“He’s got a pulse. Call an ambo.” 

The officers cleared the house as more backup arrived. Patrol started setting up tape around the house and marking evidence as paramedics loaded the injured man into the ambulance. When Hailey and Jay rejoined the group downstairs, Hank motioned for Hailey to step to aside. 

“I was with Halstead when he got the call.” Hailey began to explain. “Just figured you guys could use the help.”

“You notify Dwyer?” The Sgt asked. 

“Yes sir. Called him on the way.” Hailey responded. Hank nodded his head silently and turned to address the rest of his unit. 

“Halstead, talk to the medical examiners. Ruzek, Atwater, search the house. Try to figure out what these guys were looking for. Upton, find out who our victims are.” Hank said as he walked away from the group.

After they completed their initial run through of the crime scene, the unit had been able to identify the victims and a possible motive. A corporate lawyer, Grant Hammond, his wife Margaret and their son Ryan seemed to be killed in an attempted robbery. When a search of the house revealed a hidden stash of drugs, the unit narrowed in on this as a possible motive. Hank ordered his team to go home for the night while patrol and forensics finished processing the scene.

“Upton.” Hank called as the team began to leave. 

“Sarge.” She said when she reached him.

“Come into the district tomorrow.” He said in a way that sounded more like an order than a request. “Wear plain clothes.” 

When Hailey returned to Jay’s truck, he noticed the small grin on her face.

“What was that about?” He asked curious about what Hank had said.

“He told me to come in tomorrow.” Hailey said casually. “In plain clothes.” Jay looked over to Hailey and quirked an eyebrow. 

“You good with that?” He asked, remembering that she had turned down the job offer just a few months prior.

“With plain clothes?” She asked in a joking manner. “Always. Beats a suit any day.” She said with a chuckle knowing that was not Jay’s question. “Probably just wants me to fill out some reports since I was on scene.” She followed up; she did not want to get her hopes up. If this turned into another job offer, she would jump at the opportunity. Until then, she would help in whatever way she could. 

**Notes for the Chapter:**

> I know I said the update wouldn’t be for another week but I got this one out early! I am hoping to get these updated at least once a week but with the workforce returning to the office, I have much less free time as I used to.


	4. Chapter 4

**Notes for the Chapter:**

> Hello! Thanks for all the reviews! I am glad to hear you guys are enjoying the story. I do want to warn you, I made McGrady more unlikeable in this story than he came across on the episode (in terms of his background with Hailey). I felt like the episode didn’t give us enough information and I wanted to give a clear picture for why Hailey did not want to work with him on the case. 
> 
> Thanks again to my beta reader Leigh0723 for your insights and catching my typos/grammar errors! And of course the Let's Talk Upstead tumblr group for all the conversation and support.

When Hailey arrived the next morning, she found Kim and Antonio running the background and financials for Grant Hammond. After she greeted them, she went into Hank’s office.

  
“Detective.” He said as he saw her enter.

“Sir.” She responded. She was still unsure of why she had been asked to come in.

“I spoke with Sgt. Dwyer this morning. Asked if I could borrow you for the day.” He said as he gauged her reaction. She offered a tight smile in response and a small head nod. “He said it was up to you.”

“Happy to help sir.” She responded. 

“If you could write up your reports from last night that would be helpful.” He said as he stood up and walked towards the bullpen. “Once you’re done with that, see if you can figure out where the drugs came from.” He said as he motioned for her to walk in front of him. “You can use this desk.” He said pointing her towards an empty next near Kim’s. She nodded and went to work.

She was lost in crime scene photos when a cup of coffee suddenly appeared in front of her. She looked up to see a smiling Jay leaning on her desk with his arms folded across his chest.

“I took a chance and brought you some coffee. In case you were working with us today.” He said with a cheeky grin.

“Pass up an opportunity to wear plain clothes?” She said with a smirk as she picked up the coffee. “Never.” 

Jay chuckled as he looked down at photos Hailey was sorting through. He noticed that they were pictures of the drugs they found and photos of labels from known suppliers. 

“Thank you.” She said as she drank from the coffee. Jay had placed some cream and sugar packs on her desk with the coffee. He was unsure of how she drank her coffee, so he tried to cover all his bases. He noted that she drank the coffee black. 

“What are you working on?” He asked as he picked up one of the photos.

“Trying to figure out where the drugs came from. Kim and Antonio are looking into Hammond’s finances trying to figure out if he was buying on selling.” She said as Jay nodded along. “I thought maybe I could identify the supplier from the logo on the package.” She commented with a shrug. 

“No luck?” Jay asked when he noted her uncertainty. 

“No. Kim’s looking into pods to see if they caught anyone coming in or out of the house. I thought about running Hammond’s GPS to see if that will show us where he went. Maybe he picked the drugs up directly from the supplier.” She reasoned.

“Good idea.” Jay said as he stood. He placed a hand on Hailey’s shoulder as he wished her luck and went to his desk to start working. 

A short while later, Hailey had finally been able to sort through the GPS data. She walked into the bullpen just as Kim and Antonio were sharing what they had found. 

“Guys, I think I have a lead on the supplier.” She said as she walked in. “Techs ran GPS on Hammond’s car. He had been making multiple trips to an Englewood address for a known stash house. It’s linked to a Quentin Kane. Apparently he moves a lot of product on the Gold Coast.” She said as she passed the folder with the information to Antonio. 

“Good work.” Hank said as he processed the new information. “Get the details on Kane, then get some eyes on him.” Hank directed as he turned towards his office. Hailey had began to walk towards Jay’s desk when Hank stopped.

“You’ve worked with McGrady from Narcotics, right?” He asked Hailey.

“Uh ya a few years ago on a joint investigation.” Hailey said slightly uncomfortable. 

“You should contact him and bring him in the loop. His team covers that area.” Hank suggested as he again turned to enter his office. 

“Sarge.” Hailey called before her brain had a chance to process what to say. “Makes for a crowded van.” She said with a shrug as she walked towards Hank. She stood in front of him, watched his reaction and hoped that she wouldn’t need to say more.

“You saying you got a problem with McGrady?” He asked with a surprised look on his face.

Hailey felt herself tense and tried to keep herself composed. She took a moment to figure out how to answer. 

“Yeah.” Hailey said with a soft head nod. She tried to maintain eye contact with Voight but found it difficult.

“Well, work it out. Or pack up.” He said as he motioned to the desk she was using. He turned and entered his office, shutting the door behind him. 

Hailey stood momentarily, too stunned by the exchange to move. She took a deep breath then turned to the break room, making sure not to make eye contact with anyone as she did. She went to the coffee machine and began to make herself a cup, hoping the action would help her calm down. She cursed herself for still letting McGrady interfere with her career, although this time it was completely her fault. She was pulled from her thoughts when she heard a door shut behind her. She turned to see Jay with a concerned look on his face.

“You good?” Jay asked. He had witnessed the whole exchange and noticed the change in Hailey. He could tell she was uncomfortable and from what she told him about her time with McGrady, he knew she didn’t want to work with him. He was certain there was more to the story, but even what she had shared was enough for him to understand her hesitation.

“Ya. All good.” She said running a hand through her hair. She tried to maintain a calm demeanor but internally felt her blood boiling.

“Look.” Jay said as he walked closer to her. He leaned against the counter so that he was facing her and crossed his arms in front of his chest. “I get that you don’t like working with the guy. But this is our best chance to get information on Kane.” He said in a calm voice. Hailey shook her head in response as she felt more on edge.

“It’s not that simple.” She said curtly as she glared at Jay. She watched as the hurt washed over his face. His reaction to her tone instantly calmed her down. “I’m sorry.” She said as she set down her coffee. “I didn’t mean to snap at you.”

“What’s the story with you guys?” Jay asked in a soft voice trying not to upset Hailey. “I saw you guys last night at the fundraiser.” He said, hoping that would be enough to get Hailey to open up. Hailey’s eyes widened as she realized Jay had seen her and McGrady’s encounters.

“Look, I don’t know what you think you saw-” she said defensively.

“Hailey, I saw someone that looked like they were stuck in a really uncomfortable situation that they didn’t want to be in.” He explained. Jay suddenly felt concerned Hailey thought he was implying something inappropriate. “I get that he messed with your career. I understand why you don’t want to work with him. But if you walk away from this case, you’re letting him do it again.” He tried to reason. “I’ve got your back. The team has your back. Voight has your back. Whatever you are worried about, it’s not happening this time.”

She knew he was right. This was Voight’s unit, and ultimately, he was the one calling the shots. There was no way McGrady would be able to jam her up this time. If she walked away simply because she didn’t want to work with someone, especially since she would not explain her reasons, it would not look good. It would make her look like she wasn’t a team player, or she held personal grudges. She stared at her cup as she made her decision. 

“I’ll call McGrady.” She said to Jay. He could see that she still had some hesitation.

“Hailey, what happened?” He asked. He knew there was a slim chance she told him, but he had to try.

Before Hailey had a chance to answer, the breakroom door opened. Al casually walked in and made his way towards the coffee machine. He noticed that there seemed to be a bit of tension in the room, but he ignored it and went about his business. Hailey step to the side so he could got to the machine. She gave Jay a small nod and smiled as she turned to leave. 

Jay knew Al had been on the force long enough to have worked with almost every unit. He decided to take a chance and find out more about McGrady.

“Do you know a McGrady over at Narcotics?” Jay asked.

“Sean McGrady?” Al responded with a quirked eyebrow. He continued talking after Jay nodded in response. “Ya.” He said as he drank from his coffee. Jay looked at him expectantly, waiting for more information that did not come.

“Care to share your experience?” Jay asked with a hint of sass in his tone.

“Care to share why you need to know?” Al shot back with an equal level of sass.

“Voight wants us to work with him on the Hammond case.” Jay answered. “Wants Upton to contact him.” Jay said to which Al raised his eyebrows and nodded. Al sat at the table and continued to drink his coffee. Jay sat next to him to let him know he had no intentions of walking away.

“You asking for work? Or personal reasons?” Al asked. 

“I’m asking because I want to know what I am walking into.” Jay responded with a bit of irritation. “What do you know about him?” He added.

“My experience,” Al began “is that he’s an old school copper.” Al said with a deep breath. “The kind that thinks a woman can’t do the job as good as a man.” Al tapped his fingers on his coffee mug then took another sip. There was a short silence in the room as Jay processed the info and Al thought about how much more to say. 

“It’s also been my experience,” Al said as he stood up from the table, coffee mug still in his hand. “That he can be more friendly with ladies than he should be.” Jay’s eyes widen at the statement. “Kind of friendly that a serious cop might take offense to.” Al finished as he walked out of the breakroom.

Jay nodded his head in understanding. He could see why Hailey would have a problem working with someone like that. She was a no-nonsense cop who didn’t like to be pushed around. He knew the second she walked into the crime scene at the bank and kicked Intelligence out. It started to make sense to Jay. How uncomfortable Hailey seemed around McGrady. The way she stepped away when he would take a step towards her. He had worked with cops like that before. The kind that though female officers were more efficient in clerical roles than in the field.

He couldn’t do anything about her past, but he could make sure that McGrady kept his distance during this case. 

Hailey sat at her temporary desk while she thought about calling McGrady. She flashed back to years earlier when she worked side by side with the Sgt. It did not take her long to realize that he was a bit of a womanizer. She watched his interactions with female CIs and officers. She noticed how close he would stand to them compared to their male counterparts. She had been pulled off patrol for the joint investigation, so she wanted to make a good impression. However, she was not willing to compromise her values to do it. She made sure to keep her distance from the Sgt, made sure to maintain a professional relationship with him to avoid any unwarranted stares or assumptions. 

She worried that he would take offense, but the opposite happened. He seemed to respect her for her skill and value as an officer. In fact, she quickly became is go to when he needed something done quickly and correctly. She began to think maybe her initially impression of him as sexist was wrong. It did not even bother her when he put one of her male co-workers up for the Department Commendation Award. Yes, she did most of the heavy lifting, but she was a team player and knew that Officer Smith worked hard also. He got the job done and she could not deny that he was instrumental in a major bust they had made. 

It also did not bother her too much when Officer Davis was picked at McGrady's recommendation for an undercover operation that was sure to get him noticed by the higher ups. She did not know the details of the case, but she assumed that a man had been specifically requested for the job.

She continued to work hard at McGrady's side. She remained his go to while being sure to not socialize with him outside of work. She continued to brush off all the opportunities she was passed up for, until one for a task force came along. The agent in charge had personally contacted her asking if she would be interested in joining. Hailey was blown away at the offer and accepted on the spot. The agent assured her that having her leadership sign off on the move was just a formality. They were impressed with her work on the joint investigation and were ready bring her on. 

When the same agent contacted her the following week, Hailey was not prepared for the news he brought. She found out that they were going with another officer for the task force. Confused, she asked what happened to change their mind. She was surprised to hear the McGrady had told the SAC for the task force that Hailey would not be a good fit. She would get emotional over cases and seemed to have a chip on her shoulder about being a female on the force. He explained that McGrady was concerned with how her standoffish interactions with her male counterparts would affect the task force. The agent apologized to Hailey for getting her hopes up and wished her luck. 

Hailey felt her body temperature rising as she remembered what happened next. When she confronted McGrady, he had brushed her anger aside. Suddenly, all those other opportunities that had not gone her way came into focus; he was passing her for commendations because she was a woman. 

"Look." McGrady started as he stood from his desk and approached Hailey. "I get it. Being a woman on the force is hard. But you can't walk around with a chip on your shoulder." He said as he put a hand on her shoulder. "You are too aggressive, barking orders and always acting like you have to prove your better than the guys. It puts people off. " He said as he cupped her shoulder in his hand. 

Hailey stood frozen trying to process what was happening. 

"Aggressive?" She asked incredulously. "I'm a fucking cop!" She said as she brushed his hand off her and took a step back. "I'm not here to hold hands and make the office look pretty. I'm here to take down criminals and I'm damn good at it." She assertively said back. "You're passing me up for opportunities because I'm not docile enough? Cause I don’t smile and flirt back with you or the other guys on the team?" She continued. 

"Hailey, calm down." McGrady said with a chuckle. The fact that he found Hailey's anger funny made her more upset. She stood straight and stared at McGrady with contempt as he continued. "That's got nothing to do with why I don't put you up for awards." He said holding his hands up in defense. "I just don't want people to get the wrong idea."

Hailey was blown away at how casually McGrady had spoken. 

"Wrong idea about what?" She asked calmly. 

"You know how it goes. You're always volunteering for extra duties, always by my side, first through the door; if I start putting you up for awards, people will think we are sleeping together." He said with a shrug.

"If you start putting up for awards based on my job performance, people will think I’M GOOD AT MY JOB.” Hailey snapped back in response. "I'm by your side cause that's where YOU put me! I'm first through the door because YOU tell me to be!"

"Because I know you're a good cop! But Hailey, you know how the department is. They don't see you as a cop first." McGrady tried to reason with her. Hailey threw her hands in the air and turned away from her Sgt. She rubbed her head trying to think of what to do next. For his part, McGrady was left stunned and silent. After a few moments, Hailey turned calmly and took a few steps towards him. 

"I deserve that job on the task force." She said in a very calm and matter of fact manner. "You did not put me up for that assignment. They came to me because _I earned it_." She continued, making sure to emphasize that the job was not being handed to her.

McGrady stood up and puffed out his chest. He did not like being challenged, especially by a subordinate. 

" You know I’m a good cop. You said so yourself. I just want a chance to be recognized for my work." She said. "Call Agent Packer back. Tell him what you _really know_ about me.”

McGrady took a few deep breaths contemplating her request. He did not want to lose her. She was the best cop on his team, and he knew it. He knew what she said was true; she did deserve the spot on the task force. 

“I do this, people will talk. Make assumptions about-” He began.

“Not about me.” She said pointedly. “I have been nothing but professional. There is no reason anyone would doubt I got this assignment for any reason other than merit.” She knew what McGrady had implied. She also knew that he was worried about his reputation not hers. She had heard the rumors about affairs, but those had nothing to do with her.

She continued to stare McGrady down as he contemplated what she said. After a few moments, have gave a barely perceptible nod.

“I’ll call him tonight.” He said before he walked back to his desk.

Hailey shook her head to push the memory of the confrontation away. She took a couple of deep breaths to help her return to her calm, collected self. She picked up the phone and dialed.

**Notes for the Chapter:**

> I originally had the explanation to Hailey and McGrady's backstory in Chapter 5, but I decided to move it here!


	5. Chapter 5

**Notes for the Chapter:**

> Hello! Thanks for coming back for the next chapter! I had originally planned on 1-2 chapters for each episode I was going to highlight, but this episode very quickly spiraled into more! It takes a while in between chapters because as I start working on a new one, I find myself having to go back to earlier chapters to change details. As a fan of fanfic, I understand how frustrating it is to wait for WIPs to be updated. I just wanted to let you guys know that it’s not because I have abandoned the fic, I am just trying to get all my ducks in a row before posting a new chapter. Also, time is a major factor, but I try to have 2-3 chapters written out before I update so I don’t get boxed in. This chapter, for example, has changed 6 times since I first wrote it (insert face palm). Thanks to Leigh0723 for going on this ride with me! I hope you are enjoying!

"McGrady."

"Sarge. It's Detective Upton." She said hoping to stay professional.

"Hailey." He responded. There was a heavy moment of silence before he spoke again. "What can I do for you." He said with a slight hint of irritation in his voice. 

"I am working with Intelligence on an active shooter call that came in last night." She began. "We traced some drugs back to a supplier in the Englewood area."

"Quintin Kane." McGrady stated in a flat tone. 

"We traced the vics GPS to Kane’s stash house on South Racine. Voight was hoping you could loop us in on him. Possibly run surveillance with us."

"So, you're Intelligence now?" He asked with curiosity. 

"I'm still Robbery/Homicide. Just helping them out." She replied trying to hide her annoyance. 

"Let me put a file together. Set up the van; we'll need video and stills. I'll be there in 30 minutes." He said then hung up before Hailey could respond. Hailey rolled her eyes and took one more deep, calming breath before she pushed herself off her chair and went to grab Jay.

After updating the team on McGrady’s order, Jay showed Hailey to the equipment room so they could gather their surveillance gear. Jay noted the change in Hailey’s demeanor as they began to pack their gear. She was quieter than she had been that morning. The tension had returned to her shoulders and he could practically see the irritation coming off her as she loaded her bag.

Before Jay had a chance to speak, he heard laughter coming from the garage. He looked to the doorway and saw Trudy escorting McGrady to the garage.

“He’s here.” Jay said to Hailey. He noted the sharp intake of breath which overtook Hailey. She nodded her head, grabbed her bag, and followed Jay’s lead into the garage.

“Detective Halstead. This is Sgt. McGrady.” Trudy said as she made a quick introduction. Jay nodded a greeting as he gave the man a firm handshake.

“Sarge.” Hailey said with a small smile and arms crossed in front of his chest. 

“Hailey.” McGrady said as he returned a polite smile. 

“Vans out front.” Trudy said as she handed McGrady the keys then left. McGrady held an arm out for Hailey to lead the way. He turned behind her and was at her side quickly. Jay followed behind.

“This seems like old times.” McGrady said in a low voice with a hint of irritation. He shot a quick side eye at Hailey as she began to speak.

“Look.” She began, keeping her voice even and calm. “I know we’ve had our differences,” she said as she looked up to McGrady. “Let’s just focus on our jobs, keep it professional, okay?” She finished. 

“Okay.” McGrady quickly responded with a tight nod. 

Behind them Jay was watching their body language. He could not hear what was being said, and he was surprised by how much it bothered him.

“So, what do we know about Quinton Kane?” Jay asked, wanting to remind them he was there too.

Hailey and McGrady stopped walking and turned to respond to Jay.

“Well. He’s a main suspect in three homicides that I’ve been chasing.” McGrady began while fumbling with the file in his hands. “We get close but, you know, no indictment thanks to the brave ASAs.” Jay chuckles at the remark. 

“You know what flag he flies?” Jay asks.

“Yeah. It’s the 100 syndicate.” McGrady answers then continues. “He has a couple of legit businesses too.”

“Any priors?” Hailey asks.

“Mm-hmm 2.” He responds. Before Hailey and Jay have a chance to ask anymore questions, McGrady takes control of the conversation. “Listen, this is how I want to run it, ok. I’m gonna take the main eye. Hailey you handle logs. Jay, I want you to do still and video because we want to prove this is an open-air market, alright? Let’s go.” McGrady spits out in one breath before he turned and walked to the van. 

Hailey, again, felt her eyes roll and a sharp intake of breath course through her lungs. Jay instantly looked to Hailey with a look on his face which let her know he was not happy with McGrady’s attitude. 

Thankfully, the victim who survived the shooting was able to give a description of his attacker which matched Kane. That, plus the stills they had taken of Kane, was enough to arrest him and bring him in for questioning. 

When they returned to the district, Jay escorted Kane to an interrogation room while Hailey and McGrady unloaded the van. 

“Gotta say,” McGrady started, “it wasn’t as weird as I thought it was going to be doing surveillance together again.” He said with regret in his voice. Hailey looked up to him to see a small smile on his face.

“Ya.” She said in response with a small nod. She was glad it was over and she understood what McGrady had said. She had wished her time on the joint investigation had ended differently. But she also knew none of the fault could be laid at her feet.

“Look.” McGrady said as he slightly shuffled his feet. “I’m gonna dig in to this some more on my end to help find more concrete evidence. I’ve got some CIs I can shake and see if something falls loose. If I hear anything, I’ll let you know.” He said. When Hailey responded with a nod, McGrady turned and left the garage. 

McGrady called Hailey a few hours later. He asked to meet up to go over a lead his CI had given him about Kane. He didn’t go over any specific details over the phone, but he said the lead was solid. Hailey mulled it over and decided to meet with McGrady in person at a well-known diner. 

Meanwhile, Jay and Voight had finished their interrogation of Kane. They were not able to rattle Kane and didn’t have any evidence other than the shaky description Ryan had provided them. To make matters worse, after ending the interrogation of Kane, they got word Ryan had succumbed to his injuries at Med. 

With their only witness dead and no hard evidence linking Kane directly to the crime scene, Jay knew they were going to have to cut him loose soon. Just as the realization hit him, Hailey walked into the bullpen. 

“Hey.” Jay said as she walked by him. “Have you talked to McGrady?” 

“Ya. I just talked to him.” Hailey said as she looked at her phone. “He wants to meet up. Go over the case tonight.” She said casually, still focused on her phone. 

“Meet up and go over the case? Did he bring up new leads, new evidence?” Jay asked confused. If McGrady had found something that could have helped the case, he should have brought the information to the team. Jay did not understand why only Hailey would be looped in. Was this really about the case?

Hailey, noting the tone in Jay’s voice put her phone away and looked at him.

“No.” She said with a shake of her head. “He didn’t mention anything specific.” Hailey began getting her stuff together to leave. Jay watched her as she did and debated whether he should ask the question that had popped into his mind. Al’s words about McGrady were playing in his head as she turned to walk out of the bullpen. _More friendly with the ladies than he should be._

“Is this really about the case?” He asked, trying to sound casual, worried he would offend her. 

Hailey stopped in her tracks and looked up at him. Normally, that kind of question would bother her. But something about the fact that it came from Jay made her feel like it was asked in concern for her.

“I’ll see you tomorrow.” She said as she smiled at Jay. 

Jay nodded silently and sat back in his chair. He debated whether he should tag along with Hailey. On one hand, she had not asked him to go with her. She was a cop and if she thought she needed backup, she would ask for it. On the other hand, he did not like the idea of McGrady alone with Hailey. Something about him was making her uncomfortable. He did not buy her explanation for why she did not get along with McGrady. Sure, he was difficult to work with, but Hailey was visibly uncomfortable around McGrady. 

Jay tapped his fingers along his desk as weighed his options. 

_What time are you meeting McGrady?_ Jay texted her.

_10_

The response came quick and Jay wondered if an eye roll accompanied the text. He did not want her to feel like he was checking up on her, but he also wanted to make sure the meeting went well. 

_Keep me posted if there’s new info._

_Copy that._

Yup. Definitely, an eye roll. 

It was 9 in the evening by the time Hailey had arrived home. As soon as she had stepped inside her home, her phone went off. She expected another text from Jay but was disappointed to see McGrady’s name on her screen.

_Change of plans. My CI wants to meet in person. Has critical intel on Kane. You want in?_

Hailey shut her eyes as her shoulder sunk into her. She felt her head rock forward as she let out a deep sigh. She was up for meeting McGrady in a well-lit diner full of people to go over a lead, but an undisclosed location with a CI? 

She shook the hesitation out of her mind and responded to McGrady. If she wanted to nail Kane, she needed to chase down this lead with McGrady. As she sent off her message, she locked her door and turned back to her car.

_Send me the details._

_5392 South Hoyne. 1045. Meet at the liqour store on the corner of 3 rd and South Hoyne. _

Hailey looked at her watch. An hour and 45 minutes until the meet.

_I’ll be there at 10:25. Wait for me._

Hailey was thankful the meet was happening soon. She would rather get it over with than sit with her thoughts. As she got into her car, Hailey plugged the meet’s address into her GPS. The estimated arrival time from her current location to the liquor meant she had time to stop at her favorite coffee shop. As she was leaving, she remembered Jay’s request and sent him a quick text. 

_Change of plans. Meeting a CI of McGrady’s at 1045. On my way to McGrady to go over details before the meet._

Jay looked at his watch. There was over an hour until the meet. Plenty of time for him to get ready and go with her if she asked.

_What’s the location?_

_5392 South Hoyne in Englewood._

_Want me to come?_

Hailey smirked at Jay’s question. She knew it was more of a request to be invited than an actual question. 

_I’m good. I’ll update you after the meet._

_Copy_

When she was walking back to her car from the coffee shop, she felt her phone vibrate with a text message. 

_I’m here_.

Hailey looked at the time. 10:07. She rolled her eyes as she remembered McGrady’s habit of always arriving early for any meeting. He always wanted to be the first one there. 

_I’m 10 minutes out. Wait for me at the liquor store. I’m almost there_.

When Hailey was less than 3 miles to her location, she felt her shoulders tense in anticipation. She took deep breaths in and out trying to calm her nerves. She was pulled from her breathing when she heard a call come over the radio. 

_10-1 6245 squad. Shots fired at police! I’m at 5392 South Hoyne. I’ve been hit! Oh God! Officer down!_

_This is 5021 Charlie. I’m en route to the officer calling the 10-1 I will respond. I’m 5 blocks away._

Hailey slammed on her gas pedal as she raced to McGrady’s location. She glanced at her clock. 10:11. What happened? Their meet with McGrady’s CI wasn’t for another 34 minutes. She wasn’t supposed to meet McGrady for another 15 minutes. She couldn’t make sense of what had happened. Why did McGrady go in alone?

She pulled up to the location in less than 3 minutes and drove around the building looking for McGrady’s car.

_10-1 this is 5021 Charlie I’m on scene._

She called in as she got out. She approached his car with her gun out and radio in her hand. When she got to the driver’s side door, she saw the window had been shot out and McGrady slumped in his seat. She opened the door and pulled him out to the ground. She saw bleeding coming from his neck. 

_Officer down I repeat officer down._

She placed her hand over the wound on his neck and applied pressure as he stared at her. She could tell he was trying to talk, so she encouraged him to relax.

_Don’t talk Mac. It’s ok. Help’s on the way. Just stay with me._

She watched as his eyes began to slowly shut and the color in his face drain.

_Keep your eyes open Mac. Come on Mac._

She was yelling at him and trying to control her emotions when she realized he wasn’t breathing anymore. His shallow breaths had stopped, and his body had gone limp under her hands. 

Hailey could hear the ambulance sirens getting closer as she remained kneeling at McGrady’s side. Even though she knew he was gone, she kept her hands over his neck covering his wound. Before she could process what was happening, there was yelling behind her.

“Ma’am we need you to move.” She heard as she felt hands on her shoulders. She lifted her hands off McGrady and rocked back to a sitting position on the ground. She watched as the EMTs shook their heads at each other and found herself frozen. 

Hailey dropped her head to her knees and muttered to herself, “How the hell did this happen?”.

**Notes for the Chapter:**

> Thanks for reading! I hope to update again next week!


	6. Chapter 6

**Notes for the Chapter:**

> Hello! Since the last chapter was shorter and pretty came straight from the episode, I wanted to get this one up quicker. I love reading the reviews! It’s so funny that this episode stood out to so many! I feel like they could have added a lot more into it, so this chapter is definitely a detour from the events in the episode! I hope you enjoy! Thanks again to my beta Leigh0723

Jay had just turned on a game when his phone rang. He had expected Hailey to call him after her meet, but he didn’t expect it this soon. He picked up his phone and saw it was Hank calling.

“Halstead.” He answered.

“Jay. We’ve got an officer involved shooting. You need to get to 5392 South Hoyne Street.” Hank said in a tense tone.

Jay couldn’t hear anything Hank said after that. He recognized the address as the one Hailey had given him. He felt his senses blur as he tried to process what he heard. 

“Jay. JAY! Can you hear me?” Hank said impatiently.

The way Hank said his name was enough to pull him from his thoughts. 

“Upton and McGrady were meeting a CI at that location.” Jay breathed into the phone.

“I know Jay. Upton is ok but-” Hank paused as he forced the words out of his mouth. “McGrady is dead.”

Jay felt his head slowly nod in understanding. Upton is ok. 

“I’m on my way.” He finally said as he hung up. He sat for a moment and brought his hands to his head. He felt them shaking as he tried to take deep breaths to calm himself down. Suddenly, it clicked for Jay what Hank had said. Upton is ok. 

He jumped to his feet as he grabbed his boots and quickly got them on. Hailey is ok. McGrady is dead. They were supposed to be together. Whatever happened, it was not good. He grabbed his keys and ran out his door. He jumped into his truck, immediately turning on his lights and sirens then sped off to the scene. He didn’t know what happened, but he knew he wanted to get to Hailey as fast as possible.

Hailey struggled to focus on what was happening around her. She recognized words being spoken but couldn’t process exactly what they were saying. She saw blurs moving around her but couldn’t focus on the figures. She felt hands touching her but couldn’t concentrate on what they were doing. She struggled with her senses to regain control when she felt something warm and heavy across her shoulders. Suddenly, there was a bright light flashing in front of her. The light pulled her out of the daze she was in and she glanced around to get her bearings.

“Can you hear me?” Hailey heard the paramedic holding the pen light ask. She nodded in response.

“You’re going into shock. We need you to take deep breaths and try to focus on me, ok?” The paramedic softly said to Hailey. 

Shock. That made sense to Hailey. Shock is the only word she could think of to describe finding McGrady. She realized the heavy pressure on her shoulders was a shock blanket. She looked down at her hands and stared at the blood as the paramedic pulled the blanket tighter around her shoulders.

“Are you injured at all?” She asked.

“No.” Hailey said in a whisper. The paramedic nodded and gave Hailey a shoulder squeeze.

“There are officers waiting to talk to you. Do you want to go to Med, or do you want me to send them over?” 

“It’s ok. Send them over.” Hailey answered. When she looked up, she was relieved to see Adam walking towards her. At least it was someone she knew.

“Hey Upton.” He said softly as he sat next to her. She nodded in response, still unable to turn away from her hands. “Are you ok?”

“It’s not mine.” She said as she continued to stare at the blood staining her hands. 

Adam put his arm around her shoulder and pulled the shock blanket tighter around her. Even though he barely knew Hailey, he was taken back by how small she looked in the back of the ambulance. 

“It’s just a little bit of shock, you’ll be ok.” He said softly as he watched her face. Hailey nodded and turned to look at him. 

“I need to ask you what happened. You good with that?” Hailey’s nod in response to Adam was barely noticeable.

Her eyes were drawn back to her hands as she began to speak with a shaky breath.

“I don’t know what happened.” Hailey said as she shook her head and felt her eyes tear up. She cleared her throat and started again. “We were meeting a CI. We were meeting early to scope out the location, make sure it was safe.” The more she talked the more desperation Adam could hear in her voice. 

“He was supposed to wait for me.” She said pointedly. “We were supposed to meet at the liquor store at 10:

25 and then come to this location together. He was supposed to wait for me. Why didn’t he wait for me?” The desperate look on her face was a gut punch to Adam.

It was always hard when a cop was killed in the line of duty, but for that cop to be someone you know? To be the one who finds them seconds too late? That wasn’t something Adam wished on anyone.

“I heard the call come in; I responded. I was less than 3 minutes away. When I got here the only car was McGrady’s.” Hailey’s eyes moved from Adam towards McGrady’s car. She took a deep breath in and tried to compose herself. “I didn’t see anyone else or any vehicles fleeing the scene. I walked around to the driver side of the door and saw the window shot out. When I opened the door, I found Mac.” Hailey felt her chest heave at the use of Mac. She realized she had also called him Mac as he lay on the ground dying in front of her. She had not called him that for years. Not since before their falling out. 

Hailey closed her eyes and tried to will her pain and emotions back down. She felt Adam’s arm around her shoulders once again and tried to focus on it to calm down. As she felt her breaths begin to even out, she heard a familiar voice calling her name. 

“Hailey!” Jay yelled as he jogged towards the ambulance. 

She opened her eyes and felt an instant relief course through her. As he approached, Jay quickly scanned Hailey over. He noticed the blood on her hands and her shirt. He recognized the blanket draped across her shoulders as one used to treat shock. He noted her pale appearance and could tell she had been crying.

As Jay stepped in front of Hailey, she looked away, eyes haunted. He looked over to Adam with a concerned look on his face. Adam softly nodded at him to let Jay know she was ok.

“I’m gonna get some info from forensics before Voight gets here.” Adam said as he gave Hailey a soft shoulder squeeze. “I’ll have an officer bring you something to change into. We are going to need your clothes for evidence.” He said softly as he stood from the ambulance. He exchanged a nod with Jay who instantly moved to sit on the ambulance with Hailey.

Jay took a deep breath in. He struggled to find the right thing to say.

“You good?” Jay asked, trying to get a read from her. 

Hailey wasn’t able to respond with words. Instead, she bit her bottom lip and nodded while she still looked away from Jay. 

“Were you there?” He asked softly; hesitantly. He still had no idea what happened, so he wanted to tread lightly. He also needed to know she wasn’t actually injured.

“No.” Hailey whispered. “He was already down when I got here.” 

Jay nodded slowly and sat in silence next to Hailey. A list of questions to ask ran through his head but he couldn’t bring himself to ask any of them. In that moment, all he wanted was to be there for Hailey. 

“Voight’s on his way in.” He paused when Hailey finally turned to look him in the eyes. He felt his breath hitch when he saw the bleakness in them. “Is there someone else you want me to call?” 

Hailey scoffed. There really wasn’t anyone to call. This wasn’t a revelation to her, but she never realized how sad it was until someone asked her. 

“Hailey?” Jay asked after she didn’t respond.

“I’m fine.” She said pointedly with a soft nod. Before Jay could follow up, they were approached by an officer with a forensics kit.

“Detective. I need to swab your hands for gunshot residue.” The officer said softly.

Hailey nodded and stuck her arms out in front of her. The officer swabbed her hands and labeled the evidence bag they went in. She pulled out another empty evidence bag as well as a shirt and jacket. 

“I need to collect your shirt and jacket. Officer Ruzek had someone bring these for you.” She said as she handed the clothes and the bag to Hailey. 

Jay noticed the blank look on Hailey’s face as she took possession of the items. When he watched her eyes scan the scene, he realized she was looking for a place to change. He stood from the ambulance and positioned himself in front of Hailey to get her attention. 

“I’m sure you can change in the ambulance.” He said. He looked to the officer collecting the clothes to make sure it was ok.

“We can do that Detective. I have to stay with you, but we can close the doors.” The officer softly said to Hailey. Hailey again nodded and stood up in the ambulance. She moved towards the back where she could sit comfortably in a seat. The officer climbed into the back with her and motioned for Jay to close the doors. 

After a few minutes, the doors swung open and the officer jumped out. She gave Jay a quick nod and left to turn in the evidence. Jay looked to Hailey and noticed she had gotten some of the color back in her face and had cleaned her hands. She appeared to be more focused than she was when he first arrived. She jumped down from the ambulance and took a deep breath in. 

When her eyes met Jay’s, she felt the tension in her shoulders relax. She gave him a soft nod which he instantly returned. Before anymore could be said, she saw Hank walking through the scene with Denny Woods. She let out a deep sigh which caused Jay to look in the same direction she was. He matched her deep sigh and put his hand behind her back.

“Let’s go.” He said which earned a confused look from Hailey. “I’ll go with you.” He explained. He wasn’t sure what Hank’s reaction would be and although he had no doubt Hailey could take care of herself, he didn’t want her to have to face him alone. 

Hailey stood in place and looked up to Jay.

“I’ll be fine.” She said to Jay. Jay nodded in understanding and dropped his hand as she began to walk. As he walked along side her towards Hank he noticed her gaze was pointed at the floor. The closer they got to Hank, the more nervous he became for Hailey.

“Are you sure you’re ok?” He asked while once again placing a reassuring hand on her shoulder. He wanted her to know he was there for her, not just emotionally but physically as well. 

“Ya, I’m ok.” She said with a sharp nod.

“Hey Jay.” Hank said as he approached the pair. “Give me a second alone with her.” 

Jay looked at Hank then back at Hailey. He was trying to get a read on her. When her saw her standing up straight and looking Voight in the eyes, he knew she was good.

“Ya, sure sarge. Let me know if you need anything.” Jay said as he gave her what he hoped was a reassuring squeeze on the shoulder then left.

“Hey.” Hailey said to Hank. He gave her a quick once over to take in her appearance. He noted the red eyes, the tense shoulders, the way her head hung. 

“Tough thing to go through. I’m sorry.” Hank said in a sympathetic tone as he shook his head. Hailey offered a nod in response and looked to the ground. She shuffled her feet in place as she waited for Hank to continue.

“But I gotta ask.” Hank said in a calm voice. “Why did you let McGrady drive in alone?” He asked. Hailey’s head jerk up as she met his eyes. 

The question made Hailey’s jaw drop. She blinked and shook her head slightly as if the act would change the words she just heard. 

“Excuse me?” She asked in a small, uncertain voice. 

“You were supposed to be working with him.” Hank said in a firm voice. 

“I was working with him.” Hailey responded with an equally firm voice. “He knew I was coming. We just got off the phone. I told him to wait for me.” She said incredulously.

“While you stopped for coffee?” Hank asked.

“He was supposed to wait for me!” Hailey snapped.

“But you were late!” He snapped back.

“That’s not fair.” Hailey said confused. “And I wasn’t late. I was ten minutes early.” She said more firmly this time.

Hank took a step towards Hailey and look her square in the eyes. Hailey felt her feet tense and she willed herself not to move. She knew her brain was trying to make her take a step back, but she wouldn’t let them. She was standing her ground.

“He’s dead Hailey.” Hank said sadly. “I don’t really care about fair.” He said before he looked away. 

Hailey stood frozen in place as she tried to process his words. Hank let out a deep breath as he turned back to her and continued. 

“Why don’t you take tomorrow off.” 

Hailey looked back at Hank with confusion.

“Is that a suggestion?” Hailey asked pointedly. Hank stared her down in response.

“It is what it is.” He said with a hint of frustration. “If we need anything, we’ll call you.” He said before he walked away.

Hailey was left stunned by the turn of events. She stood in the middle of the crime scene and tried to process what had happened. She watched as the world around her kept moving while she seemed to be frozen in time. 

“Upton?” She heard a voice say. “Hailey?” 

She turned to see Adam standing behind her with a concerned look on his face. 

“You good?” He asked.

“Ya.” She said after she cleared her throat. “You guys got everything you need from me?” She asked. She suddenly felt the urge to get as far away from the crime scene as possible.

“Ya, did you talk to Voight?” He asked.

“Ya. He said once I was done here, I should head home for the day.” She answered with a composed, measured tone. Adam looked at her confused.

“For the day? Or you going back to your unit?” He asked.

“Just taking the day.” Hailey said, not really sure what her situation was. “If you got everything you need from me, I’m gonna head out.” She hoped she sounded more confident to Adam than she did to herself. 

“We’re good. I’ll call you if we need anything else.” He said with a nod. Hailey nodded back and turned to walk away.

Hailey’s thoughts were racing through her mind as she tried to get to her car as quickly as possible without running.

_Five minutes; just give me five minutes_. Five minutes to get out of the crime scene. Five minutes to get as far down the street as she could. Five minutes to find a dark parking lot. Five minutes until she could lose it. 

Five minutes is all her brain would give her before she broke down in her car, not even 4 miles from where she found McGrady.

Back at the crime scene, Kevin filled Jay in on what they knew so far. They were discussing the case when Adam approached them.

“Voight wants us to pull McGrady’s phone records. Find out who he was talking to.” Adam said.

“Did Upton know who the CI was?” Kevin asked.

“She didn’t mention it.” Adam said with a head shake. “I’m sure if she knew she would have said something before she left.”

“She left?” Jay asked confused. He thought she would have said bye before she went.

“Ya. Voight said she was good to take some time off.” Adam said. 

Jay scanned the scene looking for Hailey to be sure she was gone. Had Hailey requested time off? Or was she sent away by Hank? Jay couldn’t spot Hailey but once his eyes landed on his sergeant, he made a beeline towards him.

“Sarge.” Jay said as he jogged up to Hank. “You sent Upton home?” Jay asked.

“We’ve got enough people here Jay.” Hank said after nodding to Jay. 

“She coming in tomorrow?” He asked confused. Besides the man who saw a black SUV leaving the scene, Hailey was the closest thing to a witness they had right now.

“I think Upton could use some down time.” Hank answered curtly. 

“Wait.” Jay said as he started to put the pieces together. “You think this is her fault?”

“I think she was supposed to meet McGrady but instead, she let him go in alone and now he is dead.” Hank answered matter of factly.

Jay shook his head at Hank’s words.

“You weren’t there. You don’t know what made McGrady go in.” Jay said, his tone harsher than it should have been.

“You weren’t there either Halstead. No one was there because she let him go in alone!” Hank said with a firm tone.

“I talked to her. She was supposed to meet him alone. He contacted her an hour and a half before the meet and changed the plan. Different plan, different time, different location for the meet. When I talked to her, she was on her way to him over an hour early!” Jay said in a defensive tone. 

“What’s this about Jay?” Hank asked as he shook his head with confusion.

“What?” Jay responded, equally confused. 

“We’ve got a dead cop here and you are worried about when Upton is reporting for work?” Hank said as he narrowed his eyes at Jay.

Jay paused and took a deep breath before responding. 

“I’m worried you’re blaming a good cop for something she had no control over.” Jay said in a calm but firm voice. “Hailey did this right. This was by the book.” Nothing about Jay in that moment was calm, but he knew he was treading on thin ice. He knew anything other than a calm would not end well for him. 

The two men were engaged in a staring contest when Kevin found them.

“Hey, Sarge?” Kevin hesitantly asked as he approached the men. He didn’t know what was going on, but he could tell from their body language it wasn’t good. Hank turned to Kevin and waited for him to continue.

“We are just about done here. We were gonna head out while forensics finishes processing the scene.” Kevin said. Hank turned back to Jay and reengaged the staring contest.

“Track down some guys from McGrady’s unit. Find out who his CI was.” Hank said before he turned back to Kevin. “I want to know where Kane was tonight.” Hank said to Kevin before walking away.

Kevin’s concerned look was waved off to Jay as he said goodnight. He let out a deep breath and pulled out his phone. He hoped for a text or voicemail from Hailey, but there was nothing. Jay didn’t take a moment to think about his next steps. With his phone up to his ear, he walked to his car and listened to the ringing on the other end.

**Notes for the Chapter:**

> Thanks for reading! I hope to update again next weekend! I know Hank may have come off harsh, but in the episode, he really wasn’t happy with her. I hope he wasn’t too OOC.


	7. Chapter 7

**Notes for the Chapter:**

> Sorry for the long wait! Life is picking up again and there just isn’t enough free time to write as I had during quarantine. I hope the longer chapter makes up for it. I hope to update again in a week or two! I hope you are enjoying and thank you to Leigh0723 for being my beta! Also, if you are looking to connect with some fellow Upstead shippers, check out the Let’s Talk Upstead group on Tumblr!!

When Hailey saw Jay’s name on her screen, she debated sending the call to voicemail. She didn’t want to talk. Not about McGrady’s death, not about the Hammond case and certainly not about being dismissed from the scene. She kept playing the last conversation with McGrady over in her head. The only relief she got was when the last conversation with Hank started playing.

The phone finally stopped ringing and Hailey felt relieved. She didn’t want to ignore Jay, but she couldn’t face anyone right now. She put a glass on her counter and poured herself a glass of whiskey. She heard her phone’s text alert go off as she downed her drink. She poured herself a second glass then opened her messages.

_If you need someone to talk to give me a call._

The text brought an unexpected wave of emotions over her. She recognized the words as the same ones she had said to him after dinner at Bartoli’s. Everything in her body was screaming at her to ignore him, but she couldn’t bring herself to do it. She drank her second glass as she stared at his name on her phone, then hit the call button.

“Halstead.”

“Hey.” She said with what she hoped was her normal tone.

“Hey, I just wanted to check on you.” He said hesitantly. He rolled his eyes at himself for not thinking of what to say before calling.

“I’m fine, Jay.” Hailey said as she played with her glass. “I’m not coming in tomorrow.” She tried to sound casual when she said it. She wasn’t sure if he knew Voight had dismissed her yet.

“Ya. I heard.” He regretted saying it when he heard the small intake of breath on the other end. The silence which followed made him second guess if calling was the right thing to do. 

“Anyways.” Hailey said to finally break the silence. “Did you guys get anything new from the scene?” 

“No.” Jay said with a sigh. He wished he had better news. “He didn’t mention anything about the intel the CI had?” Jay asked. He heard what he thought was a scoff at the other end.

“No.” Hailey said before taking a sip of her drink. "Mac didn't like to share. If he had a CI who turned over good results, he’d play them close to the vest. He didn’t like to be scooped on good intel." Hailey said with a hint of irritation. Jay noted Hailey’s use of the name Mac. They must have been on good terms at some point. Jay wondered what happened to make it go sideways.

"I don’t understand what happened.” She said as she rubbed her forehead. “I talked to him 5 minutes earlier. I told him to wait for me. He knew I was 5 minutes away.” 

“He didn’t mention anything strange? Someone lurking around? Maybe a car? A witness said they saw a black SVU in the area. Did he mention that?” Jay knew that if any of these had been mentioned, Hailey would have already told them. He also knew that she had been in shock at the scene. It was possible she could have forgotten until now.

“It was just a text.” Hailey said in barely a whisper. “All he said was ‘I’m here’.” She said as she set her glass down a little too hard on the counter. Jay could hear it from his end of the call. 

"What are you drinking?" He asked. He was more curious than concerned.

Hailey let out a deep sigh. 

"Just some whiskey." She said as she stared at her empty glass.

"That's my go to for rough days too." He shared with her. 

They sat in silence for a minute. Hailey, lost her in thoughts and Jay, trying not to push her. It was Jay this time who broke the silence.

“We are running McGrady’s phone records. I’ll let you know if anything pops, or we bring someone in.” 

“I appreciate that Jay.” Hailey answered sincerely. She wanted more than anything to figure out what had happened tonight. What made McGrady go in alone. Who they were supposed to meet. “I think I might go visit his wife, Anne, tomorrow. Offer my condolences.” She said as she thought back to her brief friendship with his wife. 

“You want company?”

“No.” Hailey said softly. “I know a lot of the cops in the unit. I’m sure I won’t be the only there.” To be honest, after her confrontation with Hank, Hailey wasn’t sure how she’d be received at McGrady’s home. If she got the cold shoulder like she did from Hank, she preferred Jay wasn’t there to see it. 

“Alright. Let me know if you change your mind.” Jay responded.

“Thanks Jay. I appreciate the check-in.” Hailey told Jay.

“No problem.” Jay responded softly. He could sense she was done talking for the night. “Goodnight.”

“Hey Jay?” Hailey said quickly before Jay was able to hang up.

“Ya?”

“Maybe next time...” she paused momentarily before throwing caution to the wind “maybe next time we can talk over drinks. In person.” She finally said. 

“Ya. Maybe we should.” He said in a hopeful voice. “Good night Hailey.”

“Night.” Hailey said then set down her phone.

She stared at her empty glass on the counter and decided she had enough for the night. 

As she got ready for bed, she tried to push her racing thoughts to the back of her mind. She knew rest would not come easy tonight, but she felt better knowing she had Jay in her corner. 

­­­­­­­­­­­­­

As the intelligence team rolled into the district the following morning, they wasted no time hunting down leads. Pod’s footage was pulled, CIs were called, phone records were pulled and the team tried to track down Kane's whereabouts. While the rest of the team was working, Hank and Al decided to meet with the Narcotics Unit to find out what McGrady was working on. 

"Captain Becker says the unit is going to be at Mac's house today." Hank said to Al. Al nodded in understanding. It was customary for the unit to visit the widow of a fallen officer in the days following his death. "They should be back in the office around 1."

"Hey Sarge?" Jay said after knocking on his door. "Pulled phone records. One of McGrady's CIs, a Damon Briggs, popped up on his UC call log. He called him a few times this week, last one coming in 2 hours before his death. I'm gonna head out, check his last known and bring him in." Jay said.

Before he could walk away, Hank called him into the office. When Hank motioned for him to shut the door, Jay felt himself tense. 

"You talk to Upton?" Hank asked while tapping on his desk. Jay looked to Al with a quirked eyebrow then back to Hank and nodded his response. He narrowed his eyes as he crossed his arms and waited for Hank's follow up.

What Jay got instead was a nod as Hank matched his narrowed eyes and crossed his arms in front of his chest. 

Al watched as Hank and Jay stared each other down. He took a deep breath, knowing neither one was going to back down first. 

"How's she holding up?" Al asked casually in a way that only Al could. After years at Hank's side, he had learned to diffuse tense situations. 

Jay softened his stance and looked to Al. 

"Confused. Can't really get a read." Jay said as he shook his head. "She said she was going to visit his widow this morning." 

Jay watched with confusion as Al and Hank gave each other a look he couldn't read. Before he could ask what was up, Hank spoke up.

"Get a BOLO out on this CI just in case he tries to skip town before you find him. I’m gonna check in with McGrady’s unit." Hank said as he grabbed his jacket. He stopped when he saw that Jay had not moved. 

"Was there something else you needed?" Hank asked with a firm tone as he put his hands in his pockets. 

Jay looked to Al with an expectant look.

"I'm gonna head out to Narcotics with Hank. See if they have anything helpful to add." Al said as he nodded to Jay. 

Jay resisted the urge to push further. Instead, he nodded in understanding to Al and left the office. 

Al stood as he let out a deep sigh. He looked to Hank who matched his sigh with a firm head shake. 

"We heading to Mac's?" Al asked even though he already knew the answer. 

When Hailey arrived on McGrady’s street, she wasn’t surprised to see all the cars parked on the street. The Sergeant was well liked in his unit and not everyone had the history with him that Hailey did. She knew over the next few days the house would have a revolving door of officers and city officials stopping by to pay their respects to the family. Hailey couldn’t begin to imagine how exhausting it would be for Anne and her boys, so she told herself she wouldn’t take up too much of her time. 

Hailey could feel the eyes of her fellow officers shooting daggers at her as she entered the residence. She tried to hold her head up as she scanned the crowd for the widow. When she saw her near the kitchen, she took a deep breath in and made her way over. She had thought all night about what she would say, but now that she was standing next to McGrady’s widow, she found herself at a loss for words.

“I’m so sorry.” Hailey finally managed to say. The fact that Anne refused to meet her eyes or acknowledge her presence did not go unnoticed by Hailey. “If there’s anything you need, anything I can do--”

Hailey stopped speaking when Anne turned sharply to face her.

“Thank you.” Anne said curtly. Hailey was taken back by the coldness in Anne’s tone and body language. She tried to remind herself that Anne was grieving, but as the woman turned away from her, she wondered if there was more than grief. 

Did she blame Hailey too?

Before Hailey could put anymore thought into the intereaction, she felt a hand on her shoulder.

“Ladies.” A man said as he walked up behind Anne and Hailey. Hailey recognized the voice as McGrady’s longtime partner Arnold. She stared straight ahead as she listened to Arnold comforting Anne. 

“Why don’t you go sit down? Have something to eat?” Arnold said after kissing Anne’s forehead. 

Hailey felt her body tense and she took a deep breath in as she prepared to face the fallen officer’s partner. She knew him from her time on the joint investigation. While she never had a problem with him, she was sure he knew the details of her falling out with McGrady. 

Arnold leaned on the countertop Hailey was standing at and watched Anne walk to her sons. He took a deep breath in and turned to Hailey. When their eyes met, Arnold looked away. Hailey could see the anger on his face and braced herself.

“Nice of you to come by, Hailey.” Arnold said as he stared down at the floor. “But I think we’re good.” He looked up and was met with a look of desperation on Hailey’s face. 

“I was on my way to meet him Arnold.” Hailey said softly. She needed him to know she didn’t let his partner go in alone. That his death was not the result of her refusing to work with him over a falling out that happened years ago. “He decided to go in early.” She said firmly as she took a step towards him.

Arnold shook his head and held his hand up for Hailey to stop. 

“I’d rather not discuss that now.” Arnold said with a firm voice as he looked Hailey in the eyes. “Not here in front of Anne.” He finished as he looked away from her.

Hailey couldn’t help the desperation in her actions. She knew the right thing to do was leave, but she needed answers.

“Look,” Hailey said in a hushed voice, “I know you guys were partners for a long time. You ever know him to go in solo like that?” She felt her breaths quicken as she stared at Arnold, waiting for a response.

Arnold stared back at Hailey and took in her appearance. He let out a deep breath then answered her.

“No.” He said pointedly. 

Hailey’s head dropped in defeat. She shook her head as she tried to run through the events of the evening again.

“He told me he was meeting a snitch--” she began to explain as Arnold took a drink, “about the gold coast murders—” Before Hailey could finish, Arnold cut her off.

“I don’t want to discuss any of this right now.” He said in a firm and irritated tone as he set his drink down. He had finally lost his patience with her and he couldn’t hide it anymore. “Just get the hell out of here.” 

Hailey took a deep breath in then turned away. Her eyes instantly met the eyes of officers in the home who had been watching her conversation with Arnold. As she walked through the crowd, she found it harder and harder to hold her head up. Instinctively, she reached into her pocket to pull out her phone. She hoped to see a text or missed called from Jay to offer some sort of distraction from the guilt.

There was nothing.

The ride to McGrady's house was quiet. It was a comfortable quiet that Hank had learned Al brought out of people. There was no tension, no expectation to speak, no awkwardness, just companionable silence. So, when Al let out a deep sigh as they pulled up to the house, he knew something was weighing on his mind. 

"What's up Al?" Hank asked.

"You came down pretty hard on Upton." Al said casually. Hank turned towards Al and found him staring out the window. 

"Mac is dead Al." Hank said in a firm but calm tone. "Anne is a widow. His kids lost their father." He said as he tried to remain calm. 

"You think Upton being there would've changed anything?" Al said as more of a statement than a question. 

"At least he would've had backup." Hank snapped back. 

"Come on Hank. He shouldn't have gone in. He knew she was on the way." Al said hoping to reason with Hank. He looked to Hank to see him staring at the people going in and out of McGrady's house. 

"You sound like Halstead." Hank said in stoic tone.

"What can I say. The kid's wise beyond his years." Al said with a smirk. Hank let out a huff of air as he shook his head and shut off his engine. 

As they approached the house, they greeted the people coming and going. They had been on the force with McGrady for a long time. 

"Seems like the only time I see a lot of these faces are when someone dies." Hank said ruefully as he remembered all the faces that had stopped by to pay their respects when Justin died. 

"These things are hard for everyone." Al said in a sympathetic tone as he squeezed Hank's shoulder. Once there was a clear path to the door, they entered and looked around for McGrady's widow.

The men found McGrady’s widow and offered their condolences. They gave her an update on the case and assured her they were working to bring down whoever had killed her husband. After a few minutes of consoling her, they excused themselves to look for McGrady’s long time partner. They found him in the kitchen, staring at photos that were held up by magnets on the fridge.

“Arnold.” Hank said to alert the man to their presence.

“Hank.” Arnold responded after taking a deep breath. “Al.” He nodded to both men then turned back to the fridge. “It’s a hell of a thing.” He said as he shook his head. Hank grunted in response as Al nodded in agreement. They knew exactly what he was talking about. McGrady, husband, father of two left for work and never came back. It is a hell of a thing.

“Captain says your unit was first to respond.” Arnold said as he took a sip of his drink. “That Upton was supposed to be with him.” He said with an irritated tone.

“She was with him.” Hank responded. Arnold instantly turned to face Hank. “She got to him as fast as she could. She was with him when he passed.” Hank said as Arnold scoffed at the statement. He took another long drink from his class and set it down on the table. He leaned against the counter with his eyes shut and shook his head.

“If she would have been there from the beginning.” Arnold said in a firm but quiet voice. He didn’t need to finish his thought.

“You got any idea who he was meeting?” Al asked. Arnold shook his head.

“We haven’t been partnered up for about a year. I moved out of Narcotics into Organized Crime.” He paused to take another drink. “I hadn’t talked to him for a couple of months.” Arnold answered with a shaky voice. Al and Hank could hear the regret in his voice. 

Al laid a hand on the man’s back to comfort him. He was living through every cop’s worst nightmare, losing a partner in the line of duty. 

“Listen.” Hank said with a sympathetic tone. “I know everything is still raw.” He nodded his head as he continued to speak. “But Upton,” Hank paused and shook his head. “This isn’t on her.” 

Arnold shut his eyes tight as he took in Hank’s words. When he first heard what happened, his initial thought was: _Why did Mac go in alone?_ He flashed back to his encounter with Hailey not more than 20 minutes ago. The look of confusion and desperation she had. The look of hurt that she was being blamed. He knew deep down that it was out of character for McGrady to go in without backup. But he needed someone to blame, and it was easier to blame Hailey than his dead partner.

Arnold took a deep breath and nodded in understanding. Hank extended his hand to shake Arnold’s. After saying their goodbyes to other officers in attendance, Hank and Al made their way back to the car. 

Before they could get in, Al’s phone began to ring. Hank opened his door and paused at the sound of the phone. He listened in as Al mumbled a few words then hung up.

“Briggs wasn't at his last known.” Al said. 

“Hmm.” Hank responded as he scratched his forehead. He thought about his confrontation with Hailey the previous night, the words he exchanged with Jay, and what Al had said to him on the drive to McGrady’s. He thought about his conversation with Arnold, and how he instinctively jumped to Hailey’s defense when he felt she was being blamed.

Al leaned against the frame of the car and waited for Hank to say something. He looked around at all the cars on the street and let out a deep sigh. He knew what Hank was thinking.

“Wouldn’t be a bad idea to bring Upton in.” Al said. He grinned when he heard Hank’s grunt in response. Hank shook his head and pulled out his phone.

When Hailey’s phone rang, she expected to see Jay’s name on her screen. She was surprised to see it was Hank calling her. Hailey stared at her phone for a moment before shaking off her doubts and answering.

“Upton.” She said as she answered.

“Hailey, it’s Hank.” He responded. “Halstead got a lead on McGrady’s phone records. He’s tracking down a CI who had called McGrady’s UC phone 2 hours before he died.” Hank paused to give Hailey a moment to process the new information. 

“What’s his name?” She asked. She knew the odds of knowing McGrady’s CI was low, but she still wanted to know.

“Damon Briggs. Head over to the district, see what you can dig up on him.” Hank said casually.

“Sir?” Hailey responded with confusion.

“Find out what we know about Briggs, call Halstead if you find anything that can help track him down.” Hank said pointedly.

“I’m on my way.” Hailey replied. When she hung up, she felt a wave of relief course through her body. 

There was nothing she could do to change McGrady’s death or the events leading up to it; nothing she could do to relieve some of her guilt. But at least now, she had a chance at figuring out what happened.


	8. Chapter 8

**Notes for the Chapter:**

> Hello! Thanks for clicking in to read this fic! I am really sorry that it has been weeks since the last update. Life caught up with me and I just recently started getting free time again. I hope this chapter was worth the wait! Huge thanks to my beta Leigh0723 for not giving up on me and to all you readers! 

Jay wasn’t expecting to see Hailey that day. He knew Hank had made her take the day off, but he also knew she was taking the shooting hard. So when he heard someone call his name as he was walking up the stairs toward the district, Hailey wasn’t who he expected to see when he turned around.

Jay took in her appearance as she walked towards him. He noted the bags under her eyes and the slightest bit of puffiness around them; tell tale signs of a restless and emotional night. The way her shoulders hung like she carried the weight of the world on them. He wasn’t sure why she was heading into the district, but was happy she was.

Hailey had noticed Jay stopped walking up the stairs once he saw her and she picked up her pace. 

“Hey.” Jay said softly as Hailey came to a stop in front of him. “How was McGrady’s?” He asked. The way Hailey stiffened at the question made him cringe internally. She tried to keep her eyes focused on Jay but couldn’t stop herself from glancing away.

“You know how those things are.” Hailey responded with a casual tone as she shrugged her shoulders. She didn’t want to tell Jay how it really was. The awkward encounter with Anne, the stares from everyone in the house, the conversation with Arnold **;** she had no desire to share any of it with anyone. 

Jay stood with his hands in his pockets as Hailey’s eyes darted around like she was looking for something to ground herself to. He wasn’t sure why, but he found himself reaching out to her. He placed a featherlight touch to her elbow which instantly got Hailey’s attention. Hailey was pulled from her racing thoughts and found herself completely focused on Jay.

“Want an update?” Jay asked as he nodded towards the building. 

“Actually, Voight sent me in to help you track down a CI.” Hailey responded. She looked down to her arm and tried to focus on the conversation, not Jay’s touch. When Jay followed her gaze, he realized he was brushing his thumb on her elbow and instantly dropped his hands. When Hailey looked up to him, he gave her a sheepish smile.

“If it’s Damon Briggs, you’re too late.” Jay said as he began to walk into the building. “Patrol picked him up a few minutes ago. I’m just waiting for them to bring him in.” Jay said as they walked into the bullpen. 

The whole team, minus Hank and Al, were moving around the room working on the case. She looked to the board and watched as Kevin was updating it with the new info they had found. McGrady’s picture was taped up, as well as Kane’s. A third picture she didn’t recognize was taped up next to some phone logs. 

“This Briggs?” She asked as she pointed to the photo. 

“Ya.” Kevin answered. “He called McGrady 3 times over the past week and was on the phone with him a couple of hours before he got shot.” 

“You think this is who we were meeting?” Hailey asked Jay who had moved over to the board.

“We are still running down Kane but according to Narcotics, this guy was a catch and release McGrady had been working. Apparently, he was about to send him back to jail.” Adam stated.

Hailey nodded as Jay handed her McGrady’s call logs from McGrady’s undercover phone and his personal phone. She saw what the rest of the team did, Briggs had called McGrady 5 minutes before McGrady called her to change their meet. This had to be the guy.

“Wanna sit in?” Jay asked as he motioned towards the interrogation rooms. “He should be here soon.”

“Yes.” Hailey answered with a firm nod.

+++++++

Hailey and Jay walked out of the interrogation room with two very different impressions of how the interview went. Briggs had told them he called McGrady because he was trying to recover money he had lent the sergeant. Jay was convinced Briggs was trying to save himself by selling them a fairy tale about a cop who was in deep with the wrong people over gambling debts. Hailey, on the other hand, believed every word of it.

“You believe this guy?” Jay asked incredulously as they walked to the gun lockers.

“I do.” Hailey said confidently as she leaned against the wall. 

“Why?” Jay asked as he continued to open his gun locker.

“The money thing. It makes sense.” Hailey answered. Jay instantly stopped what he was doing and looked at Hailey. After a brief pause, she continued. “McGrady asked me to borrow a few grand last month.” 

Jay stared at Hailey as he processed her words. He looked her up and down to try to get a read on her body language. She had her arms folded across her chest and appeared stiff. He could tell she was uncomfortable about the subject.

“You lent him money.” Jay said as more of a statement than a question. Hailey blew out an exasperated breath and tried to explain.

“I didn’t say I lent him money.” Hailey said to clarify her previous statement. “I said he asked. He sounded like he was in a really tight place.” 

“How bad?” Jay asked.

“Well,” Hailey said after a deep breath, “he likes to gamble. And he loses. A lot.” She said as she shook her head. “There’s a lot of potential suspects here.” Hailey was nervous to see how Jay reacted to her information. She wouldn’t have blamed him if he didn’t believe her, but instead, Jay nodded in understanding. Hailey let out the smallest of breaths and felt her shoulders relax at Jay’s response. 

“Ok.” Jay said with a nod. “Let’s follow up on Briggs’ Wisconsin alibi. Once we rule him out, we’ll talk to Voight.” 

Jay and Hailey were able to confirm the informant was in Wisconsin when McGrady was shot. They informed the team but before they could tell them about McGrady’s gambling, Antonio revealed a forensics match to blood found on the gun that shot McGrady.

Quentin Kane.

“Ok. Blood is blood. Let’s arrest Kane.” Hank stated.

The team jumped to their feet and began to make their way to their cars. Hailey instinctively followed Jay to his truck and got into the passenger seat. Jay paused when he put the keys in the ignition and turned to Hailey.

“Sorry. Do you mind if I ride with you?” Hailey asked when she realized she had jumped into his truck without asking first. Jay chuckled as he turned the truck on.

“I’m not used to doing all the driving.” He said as he pulled out of the parking lot. 

“Ah.” Hailey said in understanding. “I prefer shotgun. Easier to think that way.” She said as she tried to unravel all the new information they had learned. Jay quirked an eyebrow at her comment and looked over to her. Sure enough, Hailey was staring out the window and appeared to be lost in thought. 

“You ok?” Jay asked. Hailey shook her head slightly as she rubbed her forehead.

“It doesn’t make sense.” Hailey said in a quiet yet frustrated tone. “If Briggs was in Wisconsin, who were we meeting? Why would McGrady change the meet _after_ talking to Briggs.” She rambled off to Jay.

“Maybe Kane had someone call in a tip to McGrady to set him up. Maybe you were never meeting a CI.” Jay suggested in a grim tone.

“Maybe.” Hailey agreed, “but it still doesn’t explain what happened to make the meet change.” 

++++++++ 

After a rather tense standoff between Kane and SWAT, Kane was finally taken into custody. Hailey still had her doubts about what had happened, but they followed the evidence, and this is where it led. As she watched Kane being loaded into Denny Wood’s SUV, she breathed out a sigh of relief that it was over, and she could move on. 

Back at the district, she packed up the few things on her desk to be filed away with the case and prepared herself to mentally return to Homicide. She liked her unit, but they weren’t really a team. Even though she always considered herself a lone wolf, working with a unit like Intelligence made Hailey want to be on a team. 

“You heading out?” Hailey heard Al ask from his desk. She had thought she was the only one in the bullpen and was startled by his voice.

“Ya. Just packing up the files.” Hailey answered as she moved boxes to Jay’s desk.

“Woods is holding a press conference in an hour. Intelligence’s presence has been requested in attendance.” Al stated as he cut pieces of an apple off with his knife.

“I guess it’s a good thing I’m officially back with Homicide.” Hailey responded dryly. 

“It’s a good thing.” Al said in agreement. “Although, Mac’s family will be there. His wife, kids. Might be nice for them to see a friendly face.” He added.

“I’m not sure my face is the one they want to see.” Hailey responded in a quiet, almost defeated tone. 

“There’s nothing you could’ve done.” Al said as he shifted in his seat. “It was an ambush. Only thing getting there early would’ve done is upped the body count.” Hailey scoffed at his statement.

“Not everyone sees it that way.” Hailey said in a curt tone.

“Not everyone’s opinion matters.” Al replied. “You did it by the book. Some things,” he shook his head as he let out a breath, “you can’t account for.” 

Hailey nodded in understanding, trying to convince herself that Al was right. 

“These things are hard for everyone. Give people time to cool off so they can see things more clearly.” Al said as he walked past her. She knew he meant Hank. And she wanted to believe he was right.

Reluctantly, Hailey attended the press conference with the rest of the unit. None of them wanted to be there, but all of them went to support McGrady and his family. After listening to Woods congratulate himself for what seemed like forever, it was finally over, and she was ready to get out of there. 

While leaving, she spotted Anne and her boys getting into a car. She turned to walk away but then stopped herself. She thought about Al’s words, about letting people cool off. Hailey realized that Anne may not want her help now, but she might need it one day. 

“Anne.” Hailey called softly to McGrady’s widow. When Anne turned to face her, Hailey took a deep breath and tried to stay the course. “If there’s anything you need, you, the kids, please call me.”

“Thanks.” Anne finally responded. “I appreciate that.” She said with the faintest of smiles on her face. “And I **'** m sorry about the other day. I didn’t mean to be so abrupt.” Anne said to Hailey’s shock. 

Hailey had not expected an apology, nor did she think one was necessary. 

“It’s all right.” Hailey said as she shook her head.

“I just.” Anne paused and looked away from Hailey. Before continuing, she took a deep breath in and said what had been weighing on her mind. “Mac really liked you.” She said with somber smile. “He always said how smart you were. Always talked about you.” 

Hailey was once again shocked at what Anne had said. There was a time where she had also thought McGrady thought highly of her. But all that faded away when she realized he had been blocking her promotions because she was a woman, because he was worried how it would look. She understood why he worried, he had, in fact, had flings with several cops on the force. But she was never one of them, and she knew that her job performance would stand up to any scrutiny that came her way. 

“Thanks.” Hailey said. “That’s nice to know. Anything you need, let me know.” Hailey said once again as she turned to walk away.

“Actually, there is something I would like to address.” Anne said as she looked at her kids in the car. She motioned for Hailey to walk further away, not wanting the kids to hear them talk. “It seems so meaningless now, but I can **'** t let it go. Mac came home from Community Play one night, really upset. The treasurer had accused him of stealing money.” 

Hailey tried her best to act surprised. 

“That’s terrible.” Hailey managed to say as she tried to push away all the thoughts going through her head. “I’ll reach out to him. Make sure we can get it cleared up.”

“Thanks. I’d appreciate that.” Anne said with a nod.

Once Anne’s car had left, Hailey tried to piece together this new information with what she already knew. McGrady was desperate for money. He was asking friends, CIs, cops, _her,_ to lend him money. She began walking to her car with a quickened pace as she googled the information for Community Play’s treasurer. She had just made it into her car when a text came through.

_You coming to Molly’s?_

Hailey quickly typed out her response to Jay, but paused before hitting send. She did want to go get drinks, even though she wasn’t feeling social.

She thought back to her conversation with Jay the other night, the offer to talk over drinks, but she pushed those thoughts back and pressed send. Right now, she had to figure out what was going on at Community Play. She had this nagging feeling that the McGrady case hadn’t been solved.

Jay had been sitting in his truck waiting for a response from Hailey. When his phone vibrated, he felt a little twinge of excitement course through him. Once he read Hailey’s response, disappointment replaced the excitement.

_I gotta go take care of something. Another time for sure._

++++++

Hailey had hoped meeting with the treasurer from Community Play would fill in some of the missing pieces to McGrady’s death. After Briggs information about McGrady borrowing money and Anne’s revelation that he was accused of stealing from the charity, Hailey was convinced that money was somehow involved in the shooting. Unfortunately, she was left with more questions than answers. 

A quick glance at her phone told her it was barely 8 at night. She thought back to Jay’s invite to Molly’s and decided she would rather spend time with Jay than at home with her cycling thoughts of McGrady’s murder.

Intelligence sat at their usual table in Molly’s drinking beers and toasting each other for closing the case. At least, that’s what Jay thought they were doing. In reality, he was having a hard time paying attention to the conversation. Instead, his focus kept drifting between his phone and the door to Molly’s. Even though he knew Hailey wasn’t coming, he couldn’t stop looking for her in the crowd. Jay was so lost in his thoughts; he didn’t notice a couple of officers from Narcotics had come over to talk to the unit.

“Anyways, we owe you guys.” Officer Jones said. “Seriously! That was solid work getting Kane.” He finished as he pat Kevin on the back.

“It’s nice to know Intelligence had Mac’s back.” Officer Tyler added with a bitter tone. “Too bad it wasn’t one of you with him that night.”

Adam, Kevin and Jay set their beers down in unison at the comment made by the officer. When Kim saw Jay straighten his stance towards Officer Tyler, she moved quickly to his side.

“What’s that supposed to mean?” Jay asked in a curt tone.

“Nothing.” Jones injected. “Don’t mind him.” He said as he tried to pull his friend away. 

“It means that if it was you instead of Upton meeting him, he’d still be alive.” Tyler responded to Jay. “Everyone in Narcotics knows she-”

Before Tyler could finish speaking, Jay had moved directly in front of him. The action was enough to make Tyler stop. 

“Sorry.” Jones said as he moved Tyler back away from Jay. “We’re still trying to process what happened.” He added with an apologetic nod. “We’ll let you get back to your night.” He said as he motioned for Tyler to walk away. Tyler took the hint, raised his hands in defense, then walked away. 

Kim placed a hand on Jay’s arm, subtly telling him to let it go as well. Jay nodded in understanding and turned back to his drink. He tried to relax but couldn’t let the tension fall from his shoulders. He knew people were blaming Hailey, and he started to wonder if she knew it. He doubted a couple of officers would say anything to her face, but officers who had been on the job longer, officers that knew McGrady, they might. 

Jay huffed out a big sigh and turned his head towards the door just in time to see a blur or blonde hair swishing away from the building. Realizing it was Hailey, he jumped to his feet and bolted towards the door. 

“Hailey!” Jay called out as he jogged towards her. Hailey thought about ignoring him and picking up her pace. When she had arrived at Molly’s and saw all the cops inside, she decided against entering. When she heard her name called again, she stopped and turned towards Jay. “You coming in?” He asked as he gestured towards the bar.

“Uh, no.” Hailey answered sheepishly. “I thought I got a second wind, but, I’m not really feeling social.” She tried to explain. Her response was all the confirmation Jay needed. She had been receiving backlash, probably that morning at McGrady’s house. 

“I’m just gonna head home.” Hailey continued as she tried to keep her head up.

“Did you get everything taken care of?” Jay asked, hoping to change the subject. Hailey simply responded with a confused look. “You said you had something to take care of.” He explained.

“Oh.” Hailey said as she registered what he was talking about. “Umm, ya. I did.” She answered hesitantly.

“You don’t sound sure.” Jay replied after picking up on her hesitation. “You wanna talk about it?” Jay offered.

Hailey tried to think of a polite way to turn down Jay’s offer. She did want to talk about what was bothering her, but she didn’t want to reveal what she had learned. Didn’t want to make waves or come off as tarnishing a fallen cop **'** s name. But something about Jay made her feel like she could trust him. 

Hailey shuffled her feet and stared at the ground as she braced herself to tell Jay about McGrady’s problems. 

“I was doing a favor,” she started, “for Anne.” Hailey took a deep breath as she looked Jay in the eyes. “The treasurer at Community Play,” she said in a hushed voice “accused Mac of stealing money.” 

Jay’s eyes widened at the new information. He placed a hand on Hailey’s arm and guided her towards an alley where they could speak more privately. 

“From who?” Jay asked.

“From the charity. $10,ooo was missing. The treasurer found checks made out to cash. He thought it was Mac doing it.” Hailey said.

Jay ran a hand over his face trying to process what Hailey said.

“Ok. So, you think he was stealing from the charity?” Jay asked a little confused.

“Briggs said Mac was desperate to borrow money. I mean, the fact he called me and asked to borrow money is enough to convince me he was desperate.” Hailey ignored the way Jay’s eyebrow quirked at her statement and continued talking. “That night at the fundraiser, I saw Mac arguing with someone. I didn’t know who the other guy was but now I know it was the treasurer.” Hailey answered.

“Ok.” Jay said as he nodded for her to continue.

“So, the treasurer said he told Mac _that night_ he knew Mac was stealing and he was going to file a police report.” Hailey paused for Jay’s reaction. When she got none, she continued. “That’s it.” Hailey said with a frustrated shoulder shrug.

“Ok.” Jay said in a supportive tone. Hailey let out a breath of relief when Jay didn’t argue with her. “You think this is connected to his murder?”

“Yes.” Hailey answered unsure. “I think. I don’t know. I actually have no idea what any of it means. But it means something, right?” She asked Jay with a pleading tone. “I mean, he’s trying to borrow money, gets desperate enough to steal it, then he ends up dead?” 

“You think Kane killed him over a money debt?” Jay asked. Hailey pondered what he asked and couldn’t come up with an answer. She simply shook her head and shrugged her shoulders. “Kane’s blood is on McGrady’s gun.” Jay stated. “How did it get there?”

Hailey nodded and ran a hand through her hair. This was the same roadblock she kept hitting when she ran the evidence through her mind. The only explanation she could think of was one she didn’t want to say out loud. 

“What if,” Hailey paused to take a deep breath, “someone put the blood there?” She said. When she saw the flash of realization of what she was suggesting in Jay’s eyes, she instantly wanted to take it back.

Hailey looked away and braced herself for Jay’s reaction. She watched as he shuffled his feet and stared at the ground. She hadn’t known him long enough to get a read on his movements, so she stood in silence and waited for him to respond.

“If someone put it there, they’d have to get their hands on his blood and McGrady’s gun. Blood would have to be planted before the shooting.” Hailey looked up shocked at Jay’s response. Hailey nodded in agreement. “So, who would want to take out McGrady and Kane?”

Hailey took one more deep breath before she finally revealed what she was thinking. What occurred to her after talking to the treasurer and taking everything she knew about McGrady and his home life into account. 

“McGrady.”

**Notes for the Chapter:**

> I hope you enjoyed the update! I wish I could say another one is coming soon, but it may be a week or two! Thanks for reading and for keeping me motivated to finish the story!


	9. Chapter 9

**Notes for the Chapter:**

> Hello again! Thanks for coming back! I am glad you guys are enjoying the story; I very much enjoy reading your comments. A couple of notes: I skim through the details of the case because that’s not my focus. This is episode 6 of season 5 in case you want to refresh your memory! I tried to provide enough information to be able to follow the story. Also, I can not for the life of me figure out how to format lines that appear on fanfic. When I write the document, I add breaks that don’t pop up. I feel like it messes with the flow of the story so I added ‘story break’ to help. I hope that makes the story less choppy and flow better! Thanks to all the readers and my beta Leigh0723!

Jay stared at Hailey as he tried to process her suggestion. For McGrady to put Kane’s blood in his gun, he would’ve had to plan his own murder in advance. Which could only mean one thing: he killed himself.

Jay’s silence began to make Hailey feel nervous, so she started to back track.

“Or another cop.” Hailey said sheepishly. “Everyone knew we were looking at Kane for the shooting.” 

“And planting blood on the gun would help us nail him.” Jay finished. He watched Hailey nod in agreement. “What’s your gut say?” He asked.

Hailey was taken back by his question. Her gut said McGrady was behind this, but she was trying really hard not to show it. Was Jay seeing through her act?

“My gut says it was McGrady.” Hailey said in a resigned tone. To her relief, Jay nodded in agreement. “Either way, if this is a plant, they had to get the blood from somewhere. I was thinking about checking the evidence logs.” She finished. 

“Want me to come with you?” Jay asked.

Hailey thought momentarily about saying yes. It would be great to have a partner helping her untangle this mystery, but she didn’t want to drag Jay into it. 

“I think I can handle this.” Hailey said. “But thank you.” She finished as she reached out and lightly touched his arm. With that, they said their goodbyes.

The following morning, Hailey went straight to the Area Central evidence room. She was able to easily gain access, which made her more confident McGrady could have done the same. After finding McGrady’s signature on an ISP sign in sheet, she was also able to find an entry for Kane’s blood. When she checked on the sample, she found one of the vials was missing. 

(Story Break)

Upon returning to her car, Hailey thought about calling Jay. She liked being able to talk to him about her concerns and the support he offered. She pulled out her phone and opened her messages to text him then stopped. She remembered back to McGrady’s house the morning after he died. All the looks she got from the other cops; the anger directed at her for not backing up McGrady. She thought about the backlash that outing McGrady for framing Kane could cause. She thought about everything Jay had went through just months before with Morgan’s shooting. 

And she decided to leave him out of it.

Instead, Hailey called Hank. She needed to tell someone what she found, and Hank had the kind of pull and reputation on the force that she needed on her side. 

As Hank pulled up to the meet location, Hailey felt her heart beating through her chest. 

“Hailey.” Hank said in greeting. “What’s this about?”

Hailey took a deep breath and pulled out her phone. She pulled up a photo she had discretely taken in the evidence room and handed it to Voight.

“ISP sign in sheet.” Hailey said as she watched Hank look over the photo.

Hank blinked back his confusion and looked back at Hailey.

“So..” Hank asked and waited for clarification. He watched Hailey take shaky breath before she explained.

“That’s McGrady’s signature.” Hailey responded. Hank didn’t respond and continued to stare at her as he waited for more. “Quinten Kane was popped for a DUI 2 months ago. His bloods been sitting in an evidence cooler. One of the vials is missing.” Hailey said confidently. Even though she was nervous about accusing McGrady of framing Kane, she knew she had the evidence to back it up. 

Hank narrowed his eyes at her and tried to process what she said. 

“Your saying McGrady stole Kane’s blood?” He asked.

“Yes.” Hailey responded pointedly.

“Why **?** ” Hank asked in disbelief.

“So he could frame him.” Hailey answered.

“For his murder?”

Hailey shook her head firmly and answered Hank.

“For his suicide.”

Suddenly, everything clicked for Hank. Hailey could see it all come into focus for him and he ran a hand over his face and looked away from her. She gave him a chance to process everything before she continued.

“The treasurer at Community Play told ***** accused him of stealing 10 grand. He was planning on filing a police report.”

“Mac knew this?” Hank asked.

“He told Mac the night before he died.” She answered. Once again, Hailey was left standing in silence as she waited for Hank to process the information. Finally, he looked towards his car then back to her.

“Can you sit on this?” Hank asked a shocked Hailey. “Just, give me a day to check this out. See where we go from here?”

Despite her initial shock, Hailey understood where Hank was coming from. She was, after all, asking to reveal evidence that a dead police officer stole from a charity then framed someone for his suicide to cover it all up. This was going to make waves all the way up the Ivory Tower, and Hank wanted to have all the facts before doing that. 

“Ya. I can wait.” She responded with a slightly disappointed tone. 

The disappointment in her voice didn’t go unnoticed by Hank. He simply nodded in understanding and left. 

(Story Break)

Hailey was back at Robbery Homicide the next day. She easily fell back into her old routine and tried to put the previous week behind her. All she had left to do was go to the funeral and talk to Hank. Then she could finally close the book on McGrady and move on. She spent the previous day checking her phone every 10 minutes waiting to see if Hank had called and avoiding Jay. He had messaged a couple of times asking her what she found and if everything was ok. Hailey wanted to tell him, but she also wanted to honor her words to Hank. She wanted to give him the time he asked for. After the third message from Jay, Hailey finally told him they’d talk after the funeral. That seemed to be enough to hold him off. 

Hailey was able to leave work earlier than usual so she could attend the funeral. She had brought her dress blues with her to the office and put little time or fanfare into her appearance. She waited until the last minute to get ready, hoping to arrive at the church late enough to sneak in the back but early enough to be there for the start. She was grateful that her plan worked out perfectly. 

When Hailey arrived, she saw the Intelligence Unit already seated towards the middle of the church. She noticed an empty space between Jay and Kevin and wondered if it was for her. The thought warmed her heart, but not enough to approach them. Instead, she decided to sit in the back of the church, out of view from everyone and hopefully out of range for dirty looks. 

Hailey was hoping to make it out of the cemetery unnoticed, but before she could make her getaway, she made eye contact with Jay. Even though he was on the other side of the crowd, his gaze was enough to stop her in her tracks. He motioned for her to wait for him as he tried to make his way to her.

“Did you get my text?” Jay asked as he got closer to Hailey. The confusion on Hailey’s face as she pulled out her phone was Jay’s answer. She felt her lips twitch in an attempt to smile when she read it.

_We have a seat for you. Find us when you get here._

“Sorry.” She said as she put her phone back in her pocket. “I came straight from work; I haven’t looked at my phone for hours.” She said apologetically.

“No worries.” Jay said with concern. “How you holding up?”

“I’m fine Jay.” Hailey said harsher than she intended. “I’m sorry, I’m just-”

“It’s ok. I get it” Jay said before Hailey could finish. 

“No. No, it’s not.” Hailey said as she shook her head. She took a deep breath as she watched the crowd disperse from the gravesite. Jay stood next to her in silence, wanting to ask about the evidence room but not wanting to push Hailey. Instead, he settled for comfortable silence to let her know he was there if she needed him. Hailey had finally turned to talk to him when they heard someone call out for Jay.

Jay looked over to see Kevin motioning towards the Unit. They had all planned on going to McGrady’s house after the funeral and didn’t want to leave Jay behind.

“See you at McGrady’s?” Jay asked. 

A small nod was Hailey’s answer.

(Story Break)

Walking into McGrady’s house after closing his case was different than earlier in the week. Last time she was here, Anne could barely look at her. Today, Anne embraced her and thanked her for taking care of the ‘favor’ she asked for. Murmured voices and dirty looks were replaced with kind smiles and pats on the back. She wasn’t sure if it was a result of closing the case, or because this time she walked in with Intelligence. 

After an hour in the house, Hailey was ready to leave. It was hard for her, hearing everyone talk about McGrady knowing what she knew. Even though she hadn’t spoken to Hank yet, she could tell this was the story she would have to get used to.

Jay was just as uncomfortable in the house as Hailey. The service had reminded him of all the military funerals he had attended over the years. He found his attention being drawn to the other side of the house where Hailey was leaning against a wall.

“How’s Upton taking all of this?” Jay heard Antonio ask. Antonio had also noticed Hailey’s unease in the house. 

“Uh.” Jay began. He wasn’t expecting to be asked about Hailey. “I’m not sure.” He answered

honestly. “She keeps a lot in.” It was then he noticed Hank and Hailey speaking with each other. Before he could make his way to them, Hailey was leaving the house. With Hank following close behind.

Hailey could feel Hank following behind her, but she continued her walk to her car refusing to turn around. Hank had been looking for the right time to talk to her about the arrangements he made with Raymond Price, and he realized there wasn’t going to be one. This was a band aid that needed to be ripped off. 

“Hailey! Hailey wait up.” Hank called out as he quickened his pace to her. Hailey reluctantly stopped and with an eyeroll, turned to face Hank. The moment she laid eyes on him she suddenly felt suffocated in her blues. She didn’t want to be in her uniform for what she knew was coming.

“So, I know I came down kind of hard on you about this coffee thing, letting McGrady go in alone.” Hank began. “So.”

“It's not really what you want to talk to me about though is it?” Hailey responded curtly as she began to walk again. The irritation in her face started to make Hank uncomfortable. She knew what he was going to say, and he was ashamed to ask her to do it.

“You and me gotta get on the same page.” Hank said calmly. He tried to make eye contact with Hailey, but she continued to avert her gaze and stared straight ahead instead. “Either we disclose this evidence, or we take it to the grave.” He finally said.

Hailey shook her head and scoffed. She knew what he was going to say, but she had hoped she was wrong. 

“Wait-” Hailey said in a frustrated tone. She stopped walking and turn to face Hank. “-doesn't it bother you that everyone looks at him like he's a hero?” She asked with disgust.

Hank takes her in. The anger in her eyes. The tension in her shoulders. The fury in her words.

He sighs and shakes his head.

“Yeah it bothers me.” Hank said in a sympathetic way. He really did understand why Hailey was upset. “McGrady was a good man.” 

“Mmm **.** ” Hailey said with an emphatic head shake. 

Hank took a deep breath then continued. “I know he wasn't perfect.” Hank said with a supportive tone. “But he was a good cop. I know that for sure cause I saw him in action. I watched what he did when the bullets were flying. And believe me-” Hank paused when he saw the tears begin to fill Hailey’s eyes. He knew he was asking too much from her, and his request wasn’t fair. But Hank was looking at a bigger picture. One he needed Hailey to see.

“Hailey he's got two kids.” Hank said to Hailey. Hailey was unable to maintain eye contact and looked away. She didn’t want to hear what he had to say. “Think about what happens to them if this gets out. All they have is his legacy. And his pension.” 

Hailey took a deep breath and tried to maintain her composure. The injustice of it all was over whelming, and she wanted no part of it.

“I mean you want to blow all that over some-” Hank paused and shook his head. He could feel the anger creep up as he thought of Quintin Kane and the carnage he left behind “Jack ass who mowed down a family of 3 over a couple of kilos of coke? **"**

Hailey looked away one more time. She knew if she didn’t, the tears would openly flow. Hank could see she was on the verge of breaking down. He hated what he asked her to do. He reached out and put an arm around her, hoping she could take from it the comfort he was trying to offer. Hailey took a moment to think about what she was going to do. She took a few more deep breaths then answered Hank. 

“To the grave.” Hailey said with disappointment. 

Hank reached out and pulled Hailey into a hug just as she began to cry. Hailey tried her best to keep her composure, but the stress of the week was taking over. Hank held her for a moment then stepped away. He laid his hands on her shoulders and looked her in the eyes.

“I know what I am asking you to do. And I am sorry.” He said one more time. Hailey nodded in understanding and walked away. She continued walking to her car but stopped when she felt her phone vibrate. She wanted to send Jay’s call to voicemail, but she owed an explanation about the evidence room.

“Hello?” Hailey asked with a hoarse voice.

“Hailey. Hey.” Jay said awkwardly. As much as he was calling to check on her, he was also calling for a distraction. Too many memories crept up on him during the funeral. He was already at a low point after Erin left and Morgan’s death, so the funeral hit him hard. “Did you leave?” He asked.

“Ya, I just got to my car.” Hailey answered apologetically. “You heading out?”

“Ya, I was going to. I wanted to see if” Jay paused momentarily from nerves “if you wanted to grab a drink and talk.” He finally said. “In person.”

Hailey chuckled at the comment. She recalled their agreement a few nights ago to have their next talk over drinks in person. She wasn’t feeling up to it but her plan to sulk in her home alone didn’t sound too appealing either.

“Ya. We can do that. Molly’s in an hour?” She asked. She didn’t ask, but she had a feeling Jay was just as anxious to get out of his uniform as she was. 

“Molly’s in an hour.” Jay said.

(Story Break)

Hailey was grateful that Molly’s was slow. It wasn’t surprising **;** it was 6pm on a Wednesday after all, but she was still worried it might be full. She didn’t feel like being out in public, but she wanted to see Jay. And inviting him over didn’t seem appropriate.

They had been sitting for a few minutes nursing whiskey when Hailey finally decided to break the silence.

“I checked out the evidence room.” She said out of nowhere. Jay instantly turned to face her. “I couldn’t find anything.” She said sadly. 

Jay nodded in understanding. He had been on the receiving end of disappointing discoveries before. He knew all too well that knowing someone is guilty and proving it are two very different things.

“Just because you didn’t find anything, doesn’t mean you weren’t right.” He said pointedly. Hailey looked up at him in surprise. “Doesn’t make sense for it to be Kane. He had an alibi. Even though the tape went missing, Adam said it was solid.” Jay continued. Hailey felt a wave of guilt course through her for lying to Jay. “This is just going to be one of those cases where you can’t prove what you know.” 

Hailey nodded in agreement as she finished her whiskey. She wanted to tell Jay the truth, that there was proof and she found it. But the shame of lying to cover for McGrady was too overpowering to come clean. Instead, she ordered another whiskey and responded.

“You think he killed himself?” She asked in a small and unsure voice.

Jay took a moment to think of her question before he answered.

“I don’t know.” Jay paused to process his thoughts. “Everyone at the funeral talked about what a good man he was. How much he loved his wife, his sons. But it doesn’t add up. Not with the stealing, the gambling, I don’t know. Maybe it’s best for his family to remember him as a good man.”

Hailey snapped. She set her drink down firmly and turned to Jay. 

“Good cop? Sure.” She said with conviction. “Good man? No. Not so much. He gambled away his savings **,** he cheated on Anne **,** tried to sabotage my career. Every time I was up for a promotion, son of a bitch did his best to jam me up.” Hailey picked up her drink and tried to calm herself down. Jay was taken back by Hailey’s statement. He knew there was history between her and McGrady, but he didn’t realize how much anger there was.

“You know what really pisses me off?” Hailey asked. She closed her eyes and tried to control her voice. “I think he killed himself. And I think he decided the night of the fundraiser that he was going to do it.” She took a deep breath and opened her eyes. Hailey paused to look at Jay. He was looking at her with such compassion in his eyes. She sighed softly and continued. 

“This whole thing feels like one last “screw you” from McGrady. He _knew_ I’d be the one to find him. He _knew_ I’d be blamed for not stopping it. He _knew_ the backlash I’d get from the brass and cops. He knew what he was doing when he asked me to meet him.” Hailey felt her voice begin to tremble and stopped talking. 

Jay didn’t know what to say so he just sat in silence. He racked his brain for something comforting to say, but he couldn’t think of anything. They sat in silence for a few more minutes letting everything Hailey had said sink in. 

“Hailey,” Jay said softly. He had hoped that the words would come to him if he started talking. Hailey looked up at him and waited for him to continue. Jay found himself unable to speak. All he could do was shake his head as he looked into her eyes. There was a sadness there that broke his heart. “I’m sorry.”

Hailey let out a deep breath and shook her head. 

“I uh,” She said as she ran a hand through her hair. “I think I’m gonna head out. I think this week is catching up to me.” She said apologetically. Jay nodded in understanding, still speechless. 

“I got this.” He said as Hailey pulled out her wallet to pay for the drinks. 

“You sure?” Hailey asked sheepishly. 

“Ya. You got Bartoli’s last time.” Jay said with a boyish grin.

“That was free.” Hailey shot back.

“Ok, you get next time then.” Jay said with a smile. 

Hailey looked away from Jay hoping to stop the blush from flashing across her face.

“I’ll get next time.” Hailey agreed. 

**Notes for the Chapter:**

> I hope you enjoyed the chapter and the changes I made! Next chapter gets into episode 7! See you guys again in a week or 2!


	10. Chapter 10

**Notes for the Chapter:**

> Hello again! Thanks for clicking in for the next chapter! I enjoy reading all the comments you guys leave! It’s so funny to read reactions to McGrady and that episode. I always felt like there was more to the McGrady/Upton storyline that we didn’t get to see. I also felt like McGrady purposely set up Hailey to find him after he killed himself. I think he did it knowing everyone would be mad at her and I imagine Hailey would’ve also realized it. Just like with my other chapters, the actual case and episode details are glossed over in this chapter! The actual episode isn’t my focus and -since this is AU- I am changing a lot of the way things happened in the episode! As always, thanks to my beta and everyone reading along!

After that night at Molly’s, Jay and Hailey didn’t see much of each other. Hailey’s case load picked up and she found herself working long days and nights. Jay on the other hand, found himself with a lighter case load. Unfortunately, this meant more free time to be alone with his demons. He tried going out with friends, spending time with Will, nights at the gym, early mornings running but no matter where he went, his past seemed to find him. He and Hailey had exchanged texts a few times; but had only ran into each other a few times.

The first time was at the courthouse. Jay was sitting on a bench outside of a courtroom wearing a suit when Hailey spotted him. He had his eyes closed and head resting against the wall behind him. Hailey felt her heart rate quicken as she walked towards him.

“Jay?” She called out once she was close to him. Jay’s head instantly shot up as he began looking around to see who called him. Hailey couldn’t help but notice the disorientated way he carried himself. Originally, she thought he was resting his head, but now she realized he was asleep. 

“Sorry,” She said once she was finally in front of him. “I didn’t mean to-”

“Hailey?” Jay asked confused as he ran a hand over his face. He rubbed his eyes and tried to shake himself awake. When he looked around, he realized he had fallen asleep in the hallway. “No-” He said trying to wave off her apology. “It’s fine.” 

While Jay tried to straighten himself out, Hailey took in his appearance. His 5 o’clock shadow was the first thing she noticed, followed by the dark circles under his eyes. 

“You got a case?” Jay asked as he rubbed his hand on the back of his neck.

“Ya. Just finished testifying. You?” Hailey asked concerned.

“Ya. Still waiting to get called in.” Jay said with a sheepish grin. Hailey wanted to ask if he was ok but knew this wasn’t the right time.

“Uh, I gotta head out.” Hailey said reluctantly. “But if you are free tonight, maybe we can grab some drinks?” She asked with a head tilt and a smile that made Jay instantly smile. He wanted to say yes, but he couldn’t bring himself to. He wasn’t good company lately.

“I’m sorry.” He said with a soft a head shake. “It’s not a good time for me. But another time?” He asked hopeful. 

“Another time.” Hailey said with a smile as she left.

The second time they ran into each other was next to the hostess stand of Bartoli’s. She was on hour 12 of her workday and decided to grab a good dinner before getting back to work. She spent a few minutes chatting with the owner and thanking him for the free cheesecake he packed up for her. 

“Hailey!” Jay said with surprise as he walked in. Hailey was equally surprised and very happy to see Jay.

“We gotta stop meeting like this.” She joked. Jay laughed along.

“I was picking up take out, but” Jay motioned over to the dining area, “since you’re here, wanna sit and eat?” He asked. 

Hailey wanted to say yes, but she was on her way back to work. She noticed that Jay actually looked worse than he did at court. It had been a week since she saw him, but he looked like the nap in the courthouse was the last time he had slept.

“I’m on my way back.” Hailey finally said, disappointed. “We caught a really bad case.” She started to explain. Jay waved her off.

“I get it.” He said sincerely. “Another time?” He asked.

“More plans to make plans?” Hailey asked with a joking tone. Jay sighed in exhaustion. “Sorry.” Hailey said apologetically. “I was just joking.”

“I know.” Jay said to reassure Hailey. “But you are right.” He said defeated.

“Look, Jay.” Hailey began. “if you need someone to talk to, or a drinking partner, you know you can call, right?” Hailey said sheepishly. She worried she had overstepped as she waited for him to respond.

“Copy that.” Jay said as he nodded his head as Hailey waved goodbye. 

(Story Break)

Jay found himself in the district late that night-or early that morning- after giving up on sleep. He thought if he was going to be awake anyway, he might as well try to be productive. He heads into the district and begins updating his CI files and tried to busy himself with paperwork. His plan worked a little too well, and he found himself getting sleepy after an hour of work. Realizing it was pointless to head home, he went into the breakroom to nap. 

He was startled awake a few hours later when Adam woke him up. Adam’s defensive posture alerted Jay to the fact that he was having a nightmare. He waved off Adam’s concern and tried to wake himself up. 

Jay left the district hoping breakfast and a cup of good coffee would wake him up. As he was sitting in his truck, he began scanning through different police frequencies. As tired as he was, he needed something to distract him. He couldn’t take another day sitting at a desk updating files; he needed action.

“All Units in 21 and units city-wide-” Jay felt his eyes close as he continued to listen. “-we have multiple calls of a man with a gun.”

Jay’s eyes shot open as he listen for the location and description of the suspect. Suddenly, he was wide awake. 

“5021 George, hold me down on that. Advising responding; plainclothes officer will be on the scene.” Jay said into his radio as he took off towards the location.

Jay quickly put on his vest as he exited the truck. After giving some orders to some patrol officers, he began making his way towards the direction everyone else was running from. As he was moving through the building, trying to clear it and locate the suspect, he heard the familiar sound of a canister rolling on the floor. He turned towards the noise and instantly realized what had been thrown. 

Jay dove to the floor just as a loud flash and bang rang out. A fog of smoke began to fill the air as Jay stood on his feet and continued moving through the area. He entered a room and found a body.

After calling for an ambulance to the scene, Jay returned to helping arriving officers clear the building. By the time they were done, the rest of the Intelligence Unit had arrived. Jay briefed Hank on what he knew.

“The way this went down, there’s gotta be more than one of them. He couldn’t have got behind me that fast.” Jay said.

“How many victims?” Hank asked.

**"** One her name is Theresa Mattel, student at Central Chicago College.” Jay said as he came to a stop. “Sarge.” He said pointedly. “The offender fired three rounds. Two center mass, one head tap. 

Hank looked at Jay with a surprised look on his face. Up until this point, he thought this was an attempt at a large scale shooting.

“Doesn’t sound like a mass shooting.” Hank responded. 

“It didn’t feel like one either. He used a military stun grenade. M84.” Jay said almost out of breath from the adrenaline wearing off. 

“So you were the first one on the scene?” Hank asked with a curious tone.

“Uh-” Jay looked away and tried to compose himself “ya. I was right around the corner.” 

“Huh.” Hank said in response. “ All right start pulling footage from the park. Let’s see where they were coming from.” Hank directed.

“Sarge.” Kim called out as she approached the men. “We have a witness who saw our victim run into the building with a kid. She also saw an offender running out with a kid over his shoulder.” Hank could tell from the look on her face that this was bigger than it seemed. 

“Any sign of the kid?” Hank asked even though he already knew the answer. 

Kim slowly shook her head. No.

“This is a kidnapping?” Hank asked incredulously.

(Story Break)

Back at the district, Jay looked through camera footage from the museum hoping to ID a suspect. As he watched the movements of the men, he realized their target was boy, not Theresa. He quickly called the team over to look at the footage and updated them on what he found. With this new information, Antonio realized the MO of the crew sounded familiar. 

“It might be a long shot-” Antonio began as he approached Jay’s desk, “but narcotics has had a bead on a kidnap and ransom crew they can’t make. Grab kids of local drug dealers, kidnap and hold for ransom. Parents don’t report cause they don’t want cops in their business.” 

“Hey boss!” Kevin calls out as he ran up the stairs into the bull pen. “We ID’d the boy. Olinsky’s on his way in with the mom right now.”

“Ok. Antonio, dig into this K&R crew, see what you can find. Jay, take Kevin and head over to the dad’s house.” Hank ordered.

The team scattered and started running down their leads. Antonio met with a CI to get more information about how the K&R team worked. He was able to find out that the team would grab a kid who was linked with a drug dealer, arrange for ransom and set up a location to make the exchange. Once the team got the money, they would release the kid. The CI didn’t know anything about the people in the crew, but he had heard one of the men had a badly burned right arm. 

Antonio quickly returned to the District and used the information they had to narrow down a suspect: Luis Vega. 

“Alright. Let’s roll a covert over to him. Get eyes on -” Hank began to issue orders but was interrupted by Jay.

“Okay, but what’s the plan?” Jay asked with irritation. “We can’t grab him on what we got,

if we pull him in they'll get spooked and kill the kid.” He added matter of factly.

“That’s why we get eyes on Luis right away.” Hank responded pointedly. 

“Or you put me under.” Jay suggested. Hank stood silently as he tried to process the suggestion. “He was a ranger. We served at the same time. I can connect with him.” Jay reasoned.

“That’s a bad idea. No.” Antonio interjected. “An undercover would heat him up. We don't have enough info and-”

“That's the point **.** I'd get it.” Jay answered incredulously. All Antonio could do was shake his head. He knew what getting too close looked like, and he was sure Jay was toeing the line. He looked back to Hank, hoping the Sergeant would back him.

Hank then looked to Al, his most trusted confidant, and Jay’s partner. He would know better than anyone else in the unit if sending Jay undercover was a good idea. 

“Al?” Hank asked. Al looked to Jay then back to Hank. He shrugged his shoulders softly. He didn’t want to be the one to make the call.

Hank looked back to Jay and thought about it. Jay was one of his best. He seemed to be slipping lately, but he had a rough few months. He looked back to Antonio who was softly shaking his head no. Hank looked back to Jay then nodded his head.

“Ok. Let’s give it shot.” He finally said. 

Jay let out a breath he was secretly holding. He didn’t like the way everything played out. It felt more like questioning his judgement and less like polling for a group consensus. He felt a wave of relief roll through his body when Hank agreed with him. 

“Let’s pull everything we have on Luis. Al, Antonio, put together an op plan. Jay, make sure your cover is good to go.” Hank said as he dismissed his team. 

Jay nodded his head firmly as he walked back to his desk. He tried to focus on his computer as he typed out an email to Area Central to confirm his paperwork for “Ryan” was intact. He felt the adrenaline begin to build up in him again as he started thinking about the op. He was ready to go tonight, but he knew they needed more time to set everything up. 

Jay tapped his pen nervously on his desk. He knew there was someone out there with a standing invitation for drinks that would understand what he was feeling. Even though he knew he would be bad company, he picked up his phone and typed out a quick text.

_You up for drinks tonight?_

Jay nervously played with his phone in his hands as he waited for a reply. When he got it, he felt all the nerves calm.

_Molly’s at 7?( I’ve been stuck here. I couldn’t think of what the interaction should be)_

(Story Break)

When Hailey arrived, she quickly found Jay sitting at a table with two drinks. She appreciated that he ordered for her but grimaced internally when she realized he had ordered whiskeys. 

Their go to for hard days. 

“I hope you don’t mind whiskey.” Jay said as Hailey approached the table. “If it’s too much I’ll take it off your hands.” He said in a defeated tone as he drank his own glass.

“No.” Hailey said with a small smile as she sat down. “I’m good with whiskey.” She assured him.

“Tough day?” Jay asked. 

Hailey blew out a dramatic breath at the question. 

“Tough case.” She responded. 

After explaining her case, Jay and Hailey fell into a comfortable conversation about being a Chicago cop. They told stories about cases they had worked, dangerous chases they had been in, the people they had worked with, and the bullets they had managed to dodge over the course of their careers. Jay quickly felt the tension from the day melting away the longer he talked with Hailey. 

While Hailey was telling a particularly intense story about a car chase her rookie year that ended with her cruiser flipping over, Jay realized he was having a good time. He laughed as she used coasters and glasses to recreate the scene and found it hard to look away from her smile. He felt his cheeks begin to ache and was grateful for the break in his tense day, even if it was short lived.

Jay grimaced when his phone began to ring. He let out a deep sigh and stood to excuse himself. 

When Jay returned to the counter, Hailey could see the tension in his face. She was having a really good time and didn’t want to ruin it, but she also wanted to make sure he was ok.

“You guys working a tough case?” Hailey finally asked. Jay looked down at his drink and nodded his head slowly.

“Kidnapping.” He finally said as he brought his drink to his lips. “This crew targets criminals. Grabs their kids and collects ransom.” He said with a head shake. “It’s the perfect setup. Parents don’t call cops, so no one knows a crime was committed.” 

Hailey shook her head. It really was the perfect setup. She understood the stress, any case involving children always felt ten times worse, but she felt like Jay was holding back.

“I heard about that from one of my CIs. They go after west side drug gangs?” Hailey asked. Jay nodded his response. 

“Got any leads?” She asked. The deep breath Jay took in let her know she was on shaky ice.

Jay nodded his head and continued.

“They were still on scene when I responded.” He said as he finished off his drink. “These guys were organized.” He said as he turned to look at Hailey. “They moved like a unit. Used military grade equipment.” Hailey nodded in understanding. She was aware of Jay’s military history and understood how this case might bring back memories of his time in the desert. “We were able to get a description on one of the guys. He’s former Ranger.”

“You guys got an angle to play?” Hailey asked. Jay hesitated before nodding.

“I’m going under. See if I can get an in with the crew.” Jay watched as Hailey’s eyebrow quirked at his statement. She nodded her head slowly and took another drink. “I served at the same time as Luis. I know what he’s going through.” Jay paused and looked down at his drink. 

Hailey hummed along. It was Jay who quirked an eyebrow this time. 

“You think it’s a bad idea?” He said. Hailey stared down at her drink while she thought about how to answer him.

“I’m neutral.” She finally said. 

“Neutral?” Jay asked curiously with a hint of confusion. 

“I’ve been worried.” Hailey quickly answered. “About you.” She said, looking him in the eyes. “You cover well Jay, but I’ve got eyes.” Hailey tried to maintain eye contact as Jay stared back at her. She blinked first, turning her gaze back to her drink when Jay’s eyes became too intense.

“I’m not sure what that means Hailey.” Jay said softly. Hailey nodded in understanding.

“How have you been sleeping Jay?” She asked as she turned to face Jay. She could tell he was not prepared for that question. “Every time I see you,-” Hailey paused when Jay made eye contact with her “you look like you haven’t slept without demons haunting you in weeks”. She said softly. Jay inhaled sharply and shuffled in his seat.

“I don’t need you questioning my judgement Hailey.” He responded curtly. He had enough of people questioning him today. 

“I’m not Jay.” Hailey said with her hand up in surrender. “Like I said, I’m just worried.” She paused as Jay stared straight ahead with a look of irritation. “Going into an undercover op…..” Hailey said as she tried to push back memories of her last assignment “things can go bad quickly.” Hailey said with a shrug.

Jay shook his head and ran a hand over his face. He was done with the day and the conversation.

“I’m gonna call it a night.” He said as he pulled out his wallet. Hailey stood and held out a hand to halt his actions.

“I’m sorry if I overstepped Jay.” Hailey said apologetically. 

“It’s fine.” He responded with a head shake. “I’m just tired. Need to get some sleep before tomorrow.” He said with a deep sigh. Hailey tried to smile reassuringly at him, but it fell flat. 

“It’s my turn.” She said motioning to the drinks. 

Jay smiled, remembering the agreement they made weeks ago. He nodded in acceptance and put his wallet back in his pocket. After paying their tab, the two awkwardly walked out of the bar. Jay felt bad about ending the evening early, but he really was exhausted. Hailey worried she had upset Jay by expressing her concern. 

“Jay-”

“Look-” They both spoke at the same time. Jay chuckled under his breath and Hailey shook her head at the awkwardness. Jay looked down to the ground as he put his hands in his pockets, then looked back up at Hailey. 

“Last undercover assignment I had,” Hailey paused while she tried to keep the memories from flooding forward “things went sideways. Fast.” She said pointedly as she watched Jay’s reaction. “I just wanted to make sure _you_ feel good to go undercover. I didn’t mean for it to come off as questioning you.” 

Jay stood silently with a look of shock on his face. He had a feeling she was going to apologize, but he didn’t realize how meaningful it would be. He realized there was a genuine concern for him behind her questions. 

“I get it.” Jay finally said softly. He looked at Hailey try to smile as she looked away from him. He could see in her eyes how much it took for her to share the little bit of insight into her past. “We’re good.” He said with a firm nod and a boyish grin. Hailey let out a sigh of relief and nodded in understanding. 

(Story Break)

The next day went by quickly for Jay. He spent most of it memorizing Luis’ file and getting his undercover story straight. Hank arranged for a couple of undercovers from Narcotics to serve as plan B in case Jay couldn’t connect with Luis. He looked out to the bullpen and watched Jay at his desk. He had also noticed over the last few weeks that Jay seemed off. He always looked tired and appeared to be on edge. He looked over to Al and motioned for him to come to his office. When Al entered, he instinctively shut the door behind him. 

“You think Halstead’s solid for tonight?” Hank asked Al nonchalantly. 

“I think he is as solid as ever.” Al responded with a head nod. “Why?”

Hank put his hands in his pockets and shrugged. 

“You get the Narcotics officers for tonight?” Al asked.

“Atwater is briefing them on the op and their roles.” Hank said with a nod. “I was thinking about putting one of ours in the bar with them.” Hank said as he looked to Al. “Just to keep him grounded.” 

Al nodded in agreement.

“You think Upton would be interested?” Al asked. If Hank was surprised at the question, he didn’t show it. He picked up the phone and dialed the Sergeant for Robbery Homicide.

The last thing Hailey was expecting when she walked into work this morning was getting a message that Hank Voight wanted to talk to her. She couldn’t imagine what he wanted to talk about, but she felt her hopes building up. Was he going to ask her to join Intelligence again? Once she settled her nerves, she dialed Hank.

“Voight.” The gravely voice answered on the second ring.

“Hey Sarge. It’s Upton.” Hailey quickly responded.

“Hailey.” Hank said. “I was hoping you could help us out with an op we’ve got going tonight.” 

Hailey felt her shoulders tense at the question. She hadn’t been undercover since her assignment with Booth. But more than that, she was worried what Jay would think. He had confided in her the night before, and now she was being asked to join. Would he think she was trying to babysit him? Would he think she called Hank and expressed concern? 

“All we need you to do is sit in a bar and watch Halstead’s back.” Hank said after sensing her hesitation. “There’s going to be two undercovers from Narcotics that will step in to help Jay if you give them the signal.”

“Ya.” Hailey answered confidently. “I can do that.” When he got his answer, he called the Unit into the bullpen.

“Alright.” Hank said as his team gathered around him. He began running over the plan, telling everyone their assignments. “Jay will approach Luis Vega inside the bar. Antonio and Kim will tail him to the bar and after he leaves, see if he leads us to any accomplices. Adam and Kevin, you guys monitor the wires and Jay’s camera. Be ready to back him up if necessary. We’ve got some undercover Narcotics that will step in if Jay needs help connecting with Luis. And I asked Upton to come in on this op. She’ll be inside the bar with Jay to signal the undercovers.” Hank finished. 

Jay’s attention was snapped from the whiteboard to Hank at the mention of Hailey’s name. His initial thought of Hailey was being sent in to babysit was instantly replaced with relief that she would be there to back him up. 

“You good working with Upton?” Hank asked after noticing the deer in headlights look on Jay’s face. 

“Ya.” Jay said with a firm head shake. Hank noticed the way the tension seemed to leave Jay as he answered. 

**Notes for the Chapter:**

> Apologies if the ending seemed abrupt. Originally there was a lot more here but when I realized I had moved in to 5k words, I moved it to the next chapter! I hope you enjoyed!


	11. Chapter 11

**Notes for the Chapter:**

> Welcome back! Thank you for reading my fic and commenting! I know so many people are not fans of the Camila arc, and I don’t blame you. I think it was necessary for Jay to hit rock bottom but I agree, it was definitely cringe worthy. I hope you guys like the route I take with this arc! As always, thank you to my beta reader Leigh0723 and to the Let’s Talk Upstead chat on tumblr!

When Jay walked into Veil, he instinctively looked around the club to find the exits. It was something he had been doing since his days in the military. Always check for places combatants could enter or exit. The next thing he did was look for his backup. His eyes quickly found Hailey, who was sitting alone at a table against the wall. He found his feet trying to lead him to her, but when he looked down to the end of the bar, he saw Luis and was back on track. 

Hailey watched as Jay and the bartender made small talk. She had only been given the basics for the op. Jay was approaching target Luis at a bar his sister worked as a bartender. If Jay needed help connecting with Luis, she was to signal undercover officers to step in. UCs would pick a fight with Luis and Jay would back him up. 

Hailey tried to ignore the way the bartender seemed to be flirting with Jay and focused on Luis. She watched him approach Jay at the bar and then walk away. When Jay turned slightly and made eye contact with her, she knew it didn’t work. Hailey looked over to the UCs and gave them the signal to step in.

Things quickly went off the rails once Luis began arguing with the officers. Rather than deescalating the situation and pulling his punches, Jay jumped into the fray with Luis. Hailey watched as he connected punches with the undercover officers and jumped up to intervene. Before she got the chance, however, a civilian had approached the men to help. Suddenly, Jay turned and punched the man in the face, knocking him to the ground. 

Hailey diverted her attention to the man on the ground as she tried to render aid. She quickly looked up to Jay and found him staring at the man in the floor. Hailey noticed the confusion in Jay’s face like he wasn’t in control when he punched the man. He looked at her apologetically before running off with Luis. 

When Hailey got to the van, she was furious.

“What the hell was that?” Hailey asked as she threw her jacket on a chair. Adam continued listening to the wire while Kevin tried to answer.

“You know how UC goes.” Kevin said with a shrug.

“He was supposed to pull his punches. Those UCs are pissed!” Hailey yelled as she sat in a chair. 

“Hey, hey! They’re on the move.” Adam suddenly said as the men got into Jay’s car and drove off. Hailey and Kevin remained seated while Adam climbed to the front of the van and began to follow them. 

Kevin and Adam continued to listen to Jay’s wire while Hailey began looking through Luis’ file. She read the discharge reports from his military service and noted the locations he fought. Korengal Valley, in particular, stood out to her, she recognized the name from news reports. Her heart went out to Luis, for what he must have seen and what he must have went through. Her attention was drawn back to the wire when she heard Camila and Jay talking about Luis.

“Is your brother ok?” Jay asked. “He seems a little-”

“Wasted?” Camila asked, finishing Jay’s question. 

“Just alcohol?” Jay asked. He wasn’t sure if it was genuine concern for a fellow Ranger that made him ask the question or if he was just doing his job.

“Excuse me?” Camila shot back at him.

“Usually it's alcohol and opiates you know.” Jay said nonchalantly. “If you’re stuck at orange all the time, Oxy’s the only thing that brings you back to white. Evens you out.” He said pointedly.

Back in the van, Hailey was listening to the wire and watching Jay’s body cam. She felt herself begin to tense at what Jay was saying. And how Camila seemed to respond.

“Numbs you out.” Camila corrected him. “But thanks for your input.” She curtly added.

“Sorry.” Jay stated when he picked up on her attitude. “I’m not trying to-”

“Pry? Give me advice? Yeah. You are.” Camila shot back at Jay.

Jay furrowed his eyebrows and began to explain himself.

“I’ve just been there.” Jay said with a shrug. “That’s all. I spent about 7 months doing nothing but drink, smoke, screw, fight.” Jay stopped himself from saying more.

Hailey stared wide eyed at the body cam screen. She couldn’t believe how casually Jay was discussing drugs and alcohol as coping mechanisms. She glanced over to Kevin and Adam who didn’t seem phased at all. 

“So.” Camila said with a cheeky smile. “Is this how you usually hit on women?”

Kevin and Adam chuckled at the question while Hailey tried to hide her irritation.

“What, it’s not working?” Jay deadpanned with cheeky grin.

Camila smiled back. 

“So.” Camila asked suggestively. “How’d you get over it?”

Jay was caught off guard by the question. He looked around the room as he tried to think of the answer. He realized then he didn't have one.

“I got no idea.” Jay answered. 

"Ya my brother," Camila shakes her head, clearly defeated, "he hasn’t come all the way back."

"I don’t think anyone ever does. I think you just kind of fill up whatever’s missing with something else.” Jay took a deep breath and looked at the ground.

Hailey sat back in the van trying to take in everything Jay said. She was angry with how the meet at Veil played out, but now she was also concerned. 

(story Break)

Once Jay wrapped up his conservation with Camila, he headed back to the district. As he drove, his thoughts raced from memories of his time in country and concern over his Hank’s reaction to what happened at Veil. He knew he hit the undercover narcs officers harder than they had agreed. He also knew an innocent bystander had caught a punch thrown by Jay, which would certainly be a problem if Hank wasn’t on Jay’s side.

As Jay was taking off his wire in the tech room, he heard the rest of the team funneling in from the garage. He looked up to see Hailey headed towards him with a look of barely concealed frustration and concern on her face. 

“How’s your hand?” Hailey asked calmly. She was anything but calm, but she hoped she could set the tone for their conversation.

“Fine.” Jay said as he continued to handle the wire equipment. He could sense the tension in Hailey as he glanced up at her and knew what she really wanted to talk about. “It was the right move.” He said defensively.

“It was a move. I’m not sure if it was right.” Hailey tried to keep her tone calm as she braced herself for the difficult part of the conversation. “I was looking over Luis’ files.” She said casually as she began to help Jay put the equipment away. “Psych history, medical, details on ops.”

Jay continued his task as he looked over to Hailey expectantly. He knew there was more and just wanted to get this conversation finished.

“He served in Iraq during the surge. Korengal Valley. Probably saw some-” Hailey was abruptly cut off.

“I did a tour there too.” Jay interjected. “I know what he saw.” He said with a resigned and distant tone.

Hailey inhaled sharply at Jay’s revelation. She knew lying was par for the course during undercover ops, but she couldn’t shake the feeling that everything Jay had said was true.

“Listen.” Hailey said as she ran a hand through her hair. She looked up to him and steadied her racing thoughts. “I heard the wire. That stuff you told Camila about when you go back. The stuff about not working through it all.” Hailey looked pleadingly at Jay. She was hoping whatever he told her would be the truth. “Is that true?”

Jay looked at her and considered lying. He considered keeping his wall up and his military career separate from his police one. But something about the way Hailey was looking at him made him want to be honest. 

Unable to voice the words, Jay simply nodded yes. 

Hailey let out a deep sigh. Her instincts were right and her worry for Jay increased.

“Jay.” Hailey began as she looked into Jay’s eyes. “I’m worried. You’re not seeing straight.” Hailey paused when Jay looked away. She couldn’t help the bite in her tone as she continued. “You went offline at the club. You punched a guy-” 

“I didn’t have a choice!” Jay said harshly.

“Yes, you did!” Hailey shot back equally harsh.

Jay turned away irritated. Hailey knew she overstepped, but it was necessary. She needed to call Jay out on his behavior. For his sake and for the sake of the missing child.

“I just want you to be careful Jay. You can’t trust this guy.” Hailey said pleadingly.

“Look.” Jay said as calmly as he could. “I appreciate the concern, Hailey.” Jay attempted to smile but it fell flat. “Really, I do. But I don’t need a babysitter.” Jay cautiously told Hailey. He was trying to be mindful of their friendship, but he had tackled his demons before on his own. He instantly broke eye contact, not wanting to see the hurt he knew would flash across her face.

Hailey stood straighter, slightly taken back at the comment. 

“Copy that.” Hailey said curtly as she steeled her emotions and left the room. As she left to return to her office, she wondered if she had pushed too hard. Maybe this was his problem to solve, on his own. She had tried a couple of times to reach out and offer a shoulder to lean on, but he had made it clear each time that he wasn’t interested in talking through his problems. He thought he had a handle on it and maybe he did. She certainly didn’t know him well enough to argue differently. 

Hailey walked up the stairs to her desk, turned on a light at her desk and powered up her computer. Before she had went to talk to Jay, Hank had made it clear he wanted the events of the meet at Veil to be written up how she thought best. He had smoothed things over with the undercover officers and had convinced the civilian that got hurt not to push the issue. Although Hank had wrapped the entire night up in a tidy bow, he left the report to Hailey.

“However you write this up, I will back you.” Hank said to Hailey after pulling her aside in the garage. “The two UCs have agreed to go along with whatever is in the report and the civilian isn’t interested in pursuing the matter.” He told her. 

Hailey grinned in appreciation and assured him she had no interest in jamming up Jay. Hank nodded in approval and gave her a shoulder squeeze before heading up to his office. Once she finished, she sent her report off to Hank and told herself to give Jay space. 

(Story Break)

Despite Jay’s best intentions, the case went bad, fast. He couldn’t make headway with Luis and had to resort to giving him real drugs to gain his trust. On top of that, the playful, flirtatious banter he had with Camila backfired on him. He found himself trying to fend off her advances at the bar one afternoon when he went looking for Luis. 

“So.” Camila said with a flirty tone as she watched Jay sit at the bar. “I heard you’ve been hanging with my brother.”

“Yup.” Jay answered casually. “Just talking out some work type things. Have you seen him?”

“Oh, so that’s why you’re here.” Camila said as she tossed her rag onto the bar top and put a hand on her hip. “For a second, I thought it was to see me.” 

Jay couldn’t help the boyish grin that crept across his face. He couldn’t remember the last time a beautiful woman so blatantly flirted with him.

“Nope.” He said with a chuckle. “It’s all about Luis. Sorry.” He said with a cheeky tone.

“Ouch.” Camila said half-heartedly. Jay chuckled at her dramatics.

“Ok.” Jay said, holding his hands up in surrender. “You know what. It’s 50% you, 50% Luis but between you and me, he’s not excited about you hanging out with an ex Ranger.” Jay hoped bringing Luis into the conversation would be enough to halt Camila’s advances but he was wrong. 

“No?” Camila feigned surprise as she leaned in until she was face to face with Jay. “Well I make my own decisions.” She said as she closed the distance between her and Jay. Before Jay could react, their lips connected, and Jay’s heart was racing. When Camila pulled away, Jay tried his best to stay focused.

“I do need to talk to him though.” Jay said hoping to get back on track.

“That’s your response.” Camila asked with a slight tone. Jay laughed nervously as he tried to focus on the mission and not the thoughts racing through his head.

“I’m sorry. I say really stupid things when beautiful women kiss me out of the blue.” Jay honestly responded. Camila’s face softened at the comment as she smiled at Jay.

“Try Donahue on Wells.” 

(Story Break)

Jay knew he should’ve arrested Luis once he got the location to the warehouse where the boy was being held, but he didn’t. He felt a responsibility to his fellow Ranger who was struggling to cope back in Chicago. He saw himself in Luis, but more so, he saw Mouse. Like Luis, Mouse had a hard time transitioning back to civilian life in Chicago. He could have easily ended up in Luis’ shoes if Jay hadn’t thrown him a lifeline. Jay wanted to do that for Luis also. He wanted to give him a chance to redeem himself. 

So, Jay convinced Luis to help him with a quick rescue op. He thought they could easily overpower whoever was holding the boy, but Jay overestimated how clear Luis’ mind was. Within a minute of exchanging gunfire with the guys in the warehouse, Luis was hit in the head. He died instantly.

Jay’s senses blurred when he saw Luis go down. He ran to him and heard muffled voices yelling, but he couldn’t make out what they were saying. He grabbed Luis and dragged him out of the line of fire and began CPR. He could hear feet scurrying around him and what he thought was his name, but he couldn’t hear over the ringing in his ears. He felt sweat dripping from his forehead as he continued to do CPR on Luis. Finally, Jay heard a very firm and loud voice yelling at him. Without thinking, he turned his head with his gun raised and pointed at the voice.

Luckily for Jay, it was Kevin who was calling him. After hearing his name for the 3rd time, Jay’s vision came into focus and he realized he was pointing a gun at his friend. He held his hands up in defense and set the gun down. Anyone else would’ve yelled at Jay but Kevin let him be. He watched as Jay sat down and ran his hands through his hair. Kevin slowly approached Luis and took his pulse. It was obvious with a gunshot wound to the head he was dead, but after seeing Jay doing CPR on Luis, Kevin thought Jay needed it to be confirmed. Kevin looked back to Jay and shook his head, letting Jay know Luis was gone. 

(Story Break)

After the warehouse was processed and Jay had finished writing his report, he found himself sitting in his truck, unsure of where to go. He held his phone in his hand and watched his finger hover over Hailey’s name. He knew he had messed up. He got too close and lost focus. Sitting with Luis, telling war stories while drinking, it had triggered something in Jay. He tried not to reveal too much truth about his past but talking to someone who knew what he was going through made it hard. He ended up opening a lot of wounds he thought had healed and all the memories of Rangers he watched died came flooding back when he saw Luis dead on the floor.

Jay wanted to call Hailey. He needed to talk to someone and the only person he wanted it to be was Hailey. But he had pushed her away. She tried to be there for him, tried to give him an outlet for all the stress and memories, but he shot her down. He wondered if she would tell him to go to hell if he called her, but he knew she wouldn’t. Which is why he put the phone away and started driving. It wasn’t fair to reach out to Hailey, so he reached out to the only other person who would understand what he was going through.

Camila. 

**Notes for the Chapter:**

> I hope you enjoyed! I hope to be back with a new update by next Friday. Remember, this is a slow burn like on the show! It won’t take until season 8 for upstead to happen but don’t expect it anytime soon in this story!


	12. Chapter 12

**Notes for the Chapter:**

> Oh gosh! I am posting this a week earlier than I had planned! So many have commented about Camila! I didn’t want to leave you guys in too much suspense! I HOPE you enjoy!

Jay woke up the next morning in a hungover haze in an apartment he didn’t instantly recognize. He sat up from the couch and looked around at the beer bottles covering the coffee table. When his eyes drifted up to the wall, he saw a photo on the wall that made the memories come flooding back.

Jay had come to Camila’s house the previous night to apologize to her. He knew she had been informed of Luis’ death, but she still had no idea what his role in it was. As Jay approached her door, he tried to brace himself for the anger he knew would come. He had, after all, lied to her and her brother. Not only that, but she had been the one to tell him where to find Luis on the day he was killed. If she had known he was a cop, she never would’ve told Jay, and Luis might still be alive. 

The door flew open seconds after Jay knocked. Seeing Camila in front of him, eyes swollen and red, tears streaming down her face, made him forget everything he had planned to say. Instead, before he could even cross the threshold, Camila had thrown herself into his arms. He held her for a few minutes in the doorway as she sobbed and asked him what happened. 

Jay spent the next few hours consoling Camila as she mourned the loss of her brother. The more time he spent holding her on her couch, the more his resolve to tell her the truth faded. As he listened to her talk about Luis’ dreams to overcome his demons and get his life back on track, the weight of Jay’s guilt got heavier, and his drinking picked up. The more Jay’s drinking picked up, the closer Camila drifted toward Jay. This time though when Camila tried to kiss him, he was able to stay firm in his resolve.

When Camila tried to kiss him this time, he was able to be firm. As much as it felt like rubbing salt in a wound, he told Camila Luis wanted more for her, better than a soldier with PTSD. Out of respect for Luis, he could not pursue a relationship with her. Camila was understandably disappointed and embarrassed, but Jay tried to assure her it had nothing to do with her. He looked at his watch and cringed when he saw the time. As he got up to leave, Camila stopped Jay and offered him the couch. As much as he wanted to leave, he knew it wasn’t the best idea to drive. 

Jay shook his head in an effort to clear his thoughts. A quick look at his watch told him he had been asleep for only 4 hours and still had plenty of time before he had to go in. Not wanting to wake Camila, Jay quietly gathered his things and snuck out of the apartment.

The drive home was graciously quick for Jay. All he wanted to do was take a hot shower and wash the guilt from the previous day off of him. As he stood under the steaming hot water, he thought of Camila. The pain she was in and his role in it. He knew from experience how hard it was to navigate the bureaucracy of the VA and wanted to help walk her through it. Even though deep down he knew he was playing with fire, Jay resolved himself to help Camila through the process and Luis’ burial. 

After Jay dried off and got dressed, he checked his phone to make sure he hadn’t missed any calls. He scrolled through the texts from his team checking in and one from Will asking what his plans for Thursday night were. Not present in his phone check: missed calls or tests from Hailey. He hadn’t heard from Hailey since their encounter in the equipment room a few days earlier, and he found this disappointing.

Jay thought back to that night in the equipment room and sighed. He had been harsh with Hailey when she was trying to make sure he was ok. Before he can travel too far down that memory, he realized he had a voicemail from an unknown number. A quick check of the message had his stomach tied in knots. The voicemail was from IAD.

_“Detective Halstead, this is Detective Stanton from IAD. I was hoping you could come in sometime tomorrow and answer a few question about an excessive use of force complaint that occurred in Veil nightclub. Please give me a call back at this number so we can set something up_.” 

Jay sat on his bed and dropped his head into his hands. He couldn’t help but chuckle at the shit show his year was turning into. He wasn’t sure if Hank knew yet, but he knew it was only a matter of time before he found out. He let out a deep breath and decided the sooner he got it over with the better. 

"Voight.” Hank said as he answered his call.

"Hank. I uh- I didn’t want to bother you with this, but I’m giving you a heads up. I just got a call from IAD.” Jay said in resigned tone.

“About what?” Hank asked, confused.

“That fight in the bar when I was undercover.” 

“The kidnapping case?” Hank asked surprised. “Who knew about that?”

“Upton, Atwater, 2 narcotics cops we used and Ruzek.” Jay said as he rubbed his forehead. 

“Ok. Keep it simple.” Hank replied matter of factly. “You were undercover, fight broke out, guy rushed at you with a beer bottle. You defended yourself.”

Jay couldn’t help the chuckle that came out of him.

“It’s scary how quickly you had that story ready.” Jay said to Hank.

“It’s what Upton put in her report.” 

“Copy that.” Jay said with a grin. He hadn’t read any of the reports on the op in Veil and since Hank never brought up the fight, Jay had completely brushed the event aside.

“Try to go in this morning. We’ll see you when you’re done.” Hank ordered before hanging up.

(Story Break)

Jay was grateful he was able to set up an appointment with IAD early that morning. Upon realizing he needed to go to Area Central for the meeting, he decided he’d pop in to see Hailey. Knowing he owed her an apology, he stopped at a bakery to grab a cup of coffee and a pastry as a peace offering. 

It was Jay’s first time in Robbery/Homicide since he met Hailey. He shook his head as he looked out at the cubicles arranged in the room and wondered how he’d find her. The sight of a swishing ponytail instantly alerted him to which desk he was looking for.

“Hey.” Jay said as he walked up to the side of Hailey’s desk.

"Jay!” Hailey said with a surprised tone. Her smile faded instantly from her face when she got a good look at Jay. Even with a smile on his face, she could easily see the sadness he was trying to hide.

Jay extended his arms to hand Hailey the coffee and pastry he had grabbed for her. 

“I wanted to say sorry.” Jay said sheepishly. “For snapping at you the other night. You were just looking out for me. And I do appreciate it.” He said.

Hailey smiles warmly at Jay as she took the treats he brought her.

“Thank you, Jay.” Hailey said with a soft tone. “Did you guys wrap up the case?” She said as she peeked into the pastry bag.

“Ya. We got the kid.” Jay responded before pausing. “Luis got caught in a crossfire.” 

Hailey looked up from her muffin wide eyed at Jay’s comment. 

“He didn’t make it.” Jay said trying to sound casual.

“Jay, I’m sorry.” Hailey said softly as she reached out to Jay. She placed a hand on his arm and gave it a little squeeze. She wanted to say so much more. Ask if he was ok, ask if Luis dying had triggered him, ask if he’s tried therapy, ask about drinks at Molly’s, but in the end, all she could do was look at the ground. 

“Anyway.” Jay said hoping to change the topic. “I gotta go. I have an appointment I gotta get to.” He said as he motioned towards the exit.

“Ya. Thanks for this.” Hailey said as she held up her muffin and coffee. “And I’m sorry. About Luis.” 

Jay nodded in thanks and turned to leave. He had just made it into the hallway when he heard Hailey calling out his name.

“Jay!” Hailey called out as she walked briskly towards him. “Look.” She paused to take a breath. The intensity in Jay’s eyes had momentarily made her forget what she wanted to say. “I know you don’t want to talk. And I’m sorry to keep bringing it up.” She said as she tilted her head and smiled sheepishly at Jay. “But seriously, if it ever gets to be too much, please, talk to someone.”

Jay smiled sadly at Hailey while he muttered a thanks and left. Hailey ran a hand over her hair as she walked back to her desk. She knew Jay wouldn't ask for help until he was ready, she just hoped it would happen before he fell too deep down the rabbit hole.

(Story Break)

Jay was able to get in and out of IAD quickly with relatively little stress. It seemed the report Hailey had submitted, combined with no complaint from the undercover officers or the civilian involved, was enough to make IAD dismiss the complaint. Jay was still confused of where it came from, but he wasn't too concerned about finding out. Right now, he was focused on getting back into the district and hopefully putting some of his guilt of Luis behind him. Just as he was walking up the stairs to the bullpen, he felt his undercover phone vibrating.

_Sorry if I made you uncomfortable last night. I appreciate you being here._

Jay instantly felt tension in his shoulders as he read the text. Camila was the last person Jay wanted apologizing to him or thanking him. If only she knew the extent of his role in her brother’s death.   
  


_No worries. Had an early morning, didn't want to wake you._

  
_I have an appointment with the VA this afternoon. Do you think you can stop by later?_

  
Jay let out a deep breath as he sat at his desk. The VA is a hard system to navigate, especially if you have no experience dealing with them. He knew the possibility of a funeral with full military honors was out of the question due to the nature of his death, but the VA’s life insurance policy would at least cover burial expenses. He told himself he could help Camila make arrangements without crossing over any lines. After that, Ryan would slowly and quietly bow out of her life.

_What time is your appointment?_

(Story Break)

It took a couple of very long days filled with endless paperwork and lot’s of help from Jay, but Camila was finally able to bury her brother after a week. Jay-or Ryan as Camila still knew him- had been by her side the entire time and she was sure she wouldn’t have been able to do it without him. 

Jay, for his part, found the more time he spent with Camila, the heavier the weight of Luis’ death felt. Camila’s grief was taking her on a rollercoaster of emotions and Jay couldn’t bring himself to walk away like he had planned. They spent some nights in her apartment, drinking or watching tv. Some nights were spent at Veil with her working behind the bar and Jay keeping her company at the counter. 

There were even a few times Jay received calls or texts from Camila asking for help because she was too drunk-or high- to drive. He didn’t enjoy this new role he had taken in her life, but he accepted it as part of his penance for his guilt. After the first few times he picked her up, she started inviting him along at the start of the evening.

Jay figured there was little harm in going with her. He thought maybe he could slow down her drinking, possibly even keep her from getting high. However, instead Jay found himself drinking with them and enjoying the anonymity of hanging out with her friends. No one asked difficult questions, and no one expected anything from him. They were just there for drinks and company, maybe the occasional bump of cocaine.

About three weeks in, Camila invited Jay to a party at a warehouse. Jay groaned at the offer, parties in warehouses really wasn’t his scene, but at the same time he nothing better to do. He had thought about calling Hailey a few times, but every time he tried, he would chicken out. He was ashamed of the life he was living. The excessive drinking plus hanging out with people while they were getting high was stuff that could get him into serious trouble. He had gotten really good at hiding from his unit, but he knew Hailey would see through him. So, he reluctantly agreed and found himself picking Camila up at midnight to head to the party.

Jay recognized a few of the faces at the party from Veil and nights when he had to pick up an inebriated Camila. But her core group of friends, Jay had gotten to know. They sat for a few hours talking and drinking. With each drink, Camila became more flirtatious with Jay and he found it harder to resist. At some point, Jay really isn’t sure when, Camila ended up on his lap while they listened to her friend Alex telling a story about a drug score gone hilariously wrong. It was during this story when Jay realized he was exhausted. A quick look at his watch let him know it was time to leave. 

“I should get going.” Jay said softly into Camila’s ear as he tried to maneuver her off his lap. In response, Camila turned in his lap and leaned in to whisper into his ear.

“Come on, stay.” Camila said in a sultry voice. The look in her eyes coupled with the way she had moved in his lap was almost enough to make Jay change his mind.

“It's 2:30 in the morning.” Jay said apologetically. “I gotta be up early.”

Camila pouted her lips and leaned in again.

“Let me show you something.” She whispered as she stood up and pulled to his feet. She gave him a pleading look as she extended her hand out to him. 

Jay knew in his gut taking her hand is a bad idea, but he’s too tired to fight. He grabs her hand as she led him towards the back of the warehouse into an empty room. Before he can say anything, Camila grabbed his neck and pulled him down to her. Jay was caught off guard by the move and found himself getting lost in the moment. Suddenly, Jay realized there was a powdery substance on his lips. He stopped and pulled away.

“Wait. What is that?” He says as he ran his tongue across his lips. “Is that coke?”

“I’m sorry.” Camila giggled as she ran a finger across her teeth. “It’s on my gums.”

Jay let out an irritated huff as he shook his head.

“I really gotta go.” He said again with less insistence than the first time.

“Mm fine.” Camila said with an understanding smile. “It’s just.” She grabbed his hands and looked up into his eyes. “Things are always better when you’re here with me.”

Something about the way she was looking at him broke Jay’s resolve. He missed being wanted, being needed. He didn’t want to be responsible anymore. 

Jay grabbed Camila and pulled her into another deep kiss. Camila didn’t miss a beat and quickly matched the intensity of his kiss. Jay began to walk her backwards until she hit a wall. They continued kissing and Jay felt her hands running over him. When he felt her tug on the waistband of his jeans, he was brought back to reality. 

Jay broke the kiss and took several steps away from her. Camila took a step towards him and looked up at him with confusion. Jay ran a hand down his face as he tried to catch his breath. He can’t believe how close he came to screwing up. 

“I’m sorry.” Jay said apologetically as he shook his head. “I can’t do this.”

Camila let out a disappointed sigh and nodded in understanding. She knew it was too good to be true. She smiled sadly at Jay as she reached out for his hand. 

“It’s ok.” Camila said as Jay grabbed her hand. “Give me a minute and I’ll head out with you?” She asked. Jay wanted to say no, all he wanted to do was get out of there. But he knew Camila was high and in no condition to get herself home safely. So he reluctantly agreed to wait for her.

As they are walking back to Camila’s friends, Jay accidentally bumped into a woman. 

“Yo Camila!” The woman said. “I’ve been looking everywhere for you.”

As Camila began talking to the woman, Jay grew even more annoyed. He had been trying to leave for 15 minutes already and didn’t want to wait any longer.

“I’m really going this time.” Jay said firmly to Camila.

“I know. I’m coming with you. Just let me say goodbye.” Camila said as she motioned towards the woman she was talking to.

Jay went outside and tried to catch his breath. He dodged a bullet just then in the back room. ' _This has to end'_ he thought to himself. Ryan must disappear from Camila’s life. Jay pulled out his phone and groaned at the time. It was 3 am and he was still waiting on Camila. 

Just as Jay was about to call Camila, he heard the sound of tires screeching, followed by a loud crash and then a woman screaming. Jay immediately ran towards the noise. When he got to the street, he saw a man trying to get out of his car.

“I didn’t see her. She just ran into the street.” The man said as he held his head.

Jay looked around the car and saw a woman lying on the street. He ordered the driver to call 9-1-1 and ran to the woman to help her. When he got a good look at her face, he realized it was the woman Camila was just talking to in the warehouse. He shook off the surprise and started checking her for injuries. To his shock, he realized she had several gunshot wounds to her chest. 

Jay took off his jacket and pressed it into her chest to try and slow the bleeding. When he looked up to her face, he saw the look that had haunted his memories for years. He recognized it instantly, he'd seen it too many times in Koregal Valley, too many times in Chicago. She knew she was dying, and she was terrified.

“You’re not alone.” Jay said desperately as he held her hand. “You’re not alone.” He watched her lips move as she tried to speak, and her eyes grow wider when she couldn’t. “You’re not alone.” He said to her as he watched the fear in her eyes dull as the life left them. 

Jay was still kneeling next to her and holding her hand when he heard someone running toward him.

“Ryan! Ryan! What happened!” Camila said as she ran toward the scene.

"I don’t know. I don’t know.” Jay said in a panic as he realized the situation he was in. “You gotta go! You can’t be here!” He said firmly.

“What can I do?” Camila asked in shock.

“No.” Jay said holding his hands out to stop Camila. “You’re high. The cops are going to be all over the place just get out of here.” He said firmly. “Go!” he yelled when Camila still didn’t move.

Jay watched as Camila ran away and tried to calm himself down. He still didn’t hear any sirens, which meant he still had time to fix this. He called the only person he knew who would understand and know what to do.

“Hank?" Jay said as he heard the receiver pick up on the other end. “I need help.”

**Notes for the Chapter:**

> If you were shaking your head during the warehouse scene and then cheering when Jay left, I accomplished my mission! I never planned to have him, and Camila hook up. Even though I thought it was necessary in the show in order for us to see how far Jay was spiraling, it always bothered me that he catfished her. If you were hoping for him and Camila to carry on the way they did on the show, I’m sorry to disappoint you. I just didn’t want Jay to spiral THAT hard. Next update won’t be for a week or two! I have to catchup now!


	13. Chapter 13

**Notes for the Chapter:**

> Hello! Thanks for clicking in! I am having a lot of fun writing this arc for Jay. Some have commented on how frustrating Jay’s behavior has been. He’s trapped in a fog of guilt, depression and PTSD. He isn’t seeing things clearly and doesn’t realize how bad is judgement is right now. If you remember the Season 5 Episode 10 plot, you know it gets worse before it gets better. Hang in there! Eventually he will see the light! I have to once again say this is an Upstead slow burn. If Upstead isn’t your ship, you will more than likely not like this story! Turn back now!

**Hello! Thanks for clicking in! I am having a lot of fun writing this arc for Jay. Some have commented on how frustrating Jay’s behavior has been. He’s trapped in a fog of guilt, depression and PTSD. He isn’t seeing things clearly and doesn’t realize how bad is judgement is right now. If you remember the Season 5 Episode 10 plot, you know it gets worse before it gets better. Hang in there! Eventually he will see the light! I have to once again say this is an Upstead slow burn. If Upstead isn’t your ship, you will more than likely not like this story! Turn back now!**

Hailey knew being the on-call detective for the Robbery/Homicide unit tonight meant she would more than likely be heading into the freezing Chicago weather at an ungodly hour of the night. If she were lucky, it would be a quiet night that gave her time to catch up on paperwork and update files. She had gone through quite a bit of work in the 4 hours she had been in her office before her radio went off.

_Robbery/Homicide_ , _do you copy?_

_Dispatch, this is Robbery/Homicide Detective Upton._

_Detective Upton, patrol requesting assistance at 16 th and Main. DOA female, multiple gunshot wounds to the chest. _

Hailey let out a sigh as she responded to the call.

_Copy that dispatch. I’m on my way._

_Be advised, there is a plain clothes detective on sight._

_Great_ , Hailey thought to herself. This could go one of two ways. The detective could be a valuable source of information and help move the case along quickly, or they could throw their weight around and muscle the case away from her. 

Hailey arrived on site just as the crime scene techs were arriving. Patrol had already started closing off the scene and she instantly noticed there was someone directing them on what to do. Hailey braced herself as she walked toward the man giving out orders. She found herself squinting her eyes in disbelief. She could’ve sworn she was staring at Jay Halstead, but she still wasn’t close enough to be sure.

“Jay?” Hailey called out once she was close enough to see him. Jay turned towards the sound of his name and was visibly surprised to see Hailey.

“Hailey?” Jay said as he quickly looked behind her to see if any other detectives arrived. “What are doing here?” He asked with a slightly surprised tone.

Hailey was slightly taken back by the question. She thought it was obvious she was responding to the call.

“Uh, I’m the on-call detective for Robbery/Homicide tonight.” Hailey said with a faint bite in her tone. “Are you the plain clothes on scene?” She asked.

“Um, ya. Ya. I called it in.” Jay said as he scratched his head and looked back to the body. He was still a bit disoriented from watching the victim die, and the last person he expected to see on the scene was Hailey.

Hailey noticed immediately something was off with Jay. He was behaving in a way that Hailey had never seen on him. She watched as his eyes darted around the scene as if he was looking for someone-or something- to jump out at him. He had barely acknowledged her presence and seemed to be annoyed by it.

“Jay?” Hailey asked softly as she took a step towards Jay. She softly placed a hand on his arm hoping to draw his focus to her. “Jay?” She asked again when he didn’t look at her. Jay turned to her when he felt her soft touch on his arm. Hailey was instantly concerned by the look on his face. “You good?” She asked.

Jay shook his head to try to get rid of the fog clouding his mind. He tried to muster a smile, something to show Hailey he was fine, but he couldn’t. Instead, he nodded yes.

“Ya. I’m fine.” Jay said. “Voight is on his way.” He added.

“Intelligence working this place?” Hailey asked as she turned back and looked at the warehouse. Jay followed her gaze with his eyes, but his mind was still playing catch up with everything that was happening. 

“Hmm?” Jay hummed in confusion to get Hailey to repeat the question.

“You guys working an angle here?” Hailey asked again this time looking Jay in the eyes. 

“Ya. No. Not really. I was meeting a CI. I found her as I was leaving.” He said pointing to the victim on the floor. Hailey watched Jay as he put his hands in his pocket. He shuffled slightly in place and continued to look at Hailey as if trying to read her thoughts. Hailey couldn’t help but feel like he was looking for a sign that she believed him. She finally nodded at him and looked around the scene.

“I’m gonna check in with patrol.” Hailey said as she motioned towards some officers who were interviewing witnesses. “I’ll hand the scene over once Voight gets here.” She said before walking away.

Jay let out a deep breath and ran his hand over the back of his neck. He had been replaying the events of the night in his head trying to figure out if he missed something. He was also trying to figure out how to explain what he was doing here without involving Camila. 

Hailey was speaking with a patrolman when she saw Hank arrive on scene. She excused herself and made her way to him to hand off the scene.

“Sargent!” Hailey called out to Hank. 

“Upton.” Hank said surprised. 

“I got called in by dispatch.” Hailey said answering the question Hank hadn’t asked. “I can hand off the scene now since you’re here.”

Hank looked at her and gave the faintest head nod. He looked over to Jay, then back to Hailey.

“You mind holding off on that?” He asked her. When she nodded yes, he motioned for her to follow him. 

Hank walked a determined path to his detective that was on scene. Jay hadn’t told him much on the phone, just that he was at a party and someone had been shot. Looking around at the where they were, Hank was confused about what kind of party Jay had been at.

“Jay.” Hank said pointedly as he approached Jay. The detective turned to the booming voice calling him. He straightened his stance and took a deep breath. “What’s going on.” 

Jay knew what Hank meant, but he couldn’t bring himself to answer.

“Female victim, two gunshot wounds to the chest.” Jay began to say before Hank cut him off.

“No Jay.” Hank said in a frustrated tone. Hailey, who was standing next to Hank, discreetly glanced over to Hank after hearing the bite in his tone. She wasn’t sure what was going on, but he was clearly pissed. “What’s going on, meaning, what the hell are you doing here.” He asked firmly. Hailey’s eyes darted to Jay who looked like he wanted to be anywhere but where he was currently standing.

Jay took another deep breath and swallowed hard. He knew Hank wasn’t going to let it go. 

“All right, so I was here.” Jay said with a firm head nod. “Working a CI.” He added. 

“What CI?” Hank asked. Jay tried to ignore the dryness in his mouth and answered the question.

“Camila Vega.” Jay answered. He paused for a moment and looked at Hailey. “From the Veil Club.” He could see the flash of recognition in Hailey’s face at the name.

“The girl from the kidnapping case?” Hailey asked with a surprised tone. She had a bad feeling about Camila after observing her and Jay on the bodycam. She brushed it off as a slight tinge of jealously, but now she knew her instincts were right. “Luis’ sister?” Jay nodded then watched Hank’s face intently looking for a reaction. 

“News to me!” Hank responded incredulously. “She on paper?”

Hailey couldn’t help the sigh that escaped her when Jay’s eyes widen slightly at Hank’s question. Jay swallowed hard, again, and tried to answer.

“No.” He finally said.

“Was the victim at the party?” Hank asked in a firm tone. Hailey watched in disbelief as Jay fumbled to answer the question. _What the hell is going on_ , she thought to herself.

“Ya, I-I believe so.” Jay said hesitantly. 

“You believe so.” Hank repeated incredulously. “You’ve been drinking.” Hank said as more of a statement than a question. “Anything else?”

“Just drinking.” Jay said in a not so convincing way. He looked Hank in the eyes while the sergeant stared him down. The intensity of Hank’s gaze made Jay nervous. _He doesn’t believe me_ , Jay thought to himself. He once again shook his head no to reaffirm his statement. 

Hank sighed deeply and looked to Hailey. Hailey’s eyes were trained on Jay’s face. She was watching every tick of expression that flew across it, trying to get a read. Hank already had his hands full with Denny Woods and Adam. He needed Al’s help to resolve that issue, and since he never replaced Erin, that left him 3 men down, 4 depending on how deep the hole Jay was falling down was.

“Intelligence is gonna take over this case.” Hank said to Hailey. Hailey nodded in agreement. “I’m still a man down, possibly two.” He said with a quick glance to Jay. “You mind working with Intelligence on this one?”

Hailey instinctively looked at Jay for a reaction. When she had first arrived on the scene, she felt like Jay didn’t want her there. Now, after everything that just happened, he looked as if he was begging her to say yes.

Hailey looked back to Hank and nodded.

“Of course.” She answered.

“Go back to the office.” Hank said as he took a step towards Jay. “Don’t talk to anyone. Write up your IPR.” He said firmly. 

“Upton, I’m gonna call your Sargent. Go work the body.” Hank directed. Hailey nodded and made her way to the victim. Hailey tried to push aside the way Jay was behaving but found it difficult. The way he struggled to answer questions, his appearance, and the fact that Hank seemed to be just as confused as she was were too much to ignore. Something was going on, and whatever it was had made Jay very nervous. 

(Story Break)

Jay spent the drive back to the district wishing he could go back in time. He knew he was playing with fire, but he just couldn’t stop himself. He had no feelings for Camila; he was drawn to her by his guilt. He could’ve walked away a long time ago, should’ve, but didn’t. Now his two worlds have collided into each other and he was desperately trying to find a way out.

He flew up the stairs and into the bullpen, ready to write his IPR. He had thought about the best way to explain what was going on. He saw a lot of drugs moving through Veil and saw an opportunity to turn out Camila as a CI for him. It wasn't completely a lie. He noticed Camila hung out with a lot of people who used drugs and had connections to that world. He was pretty sure her friend Alex was dealing out of Veil along with some other people he had seen. It had occurred to him before that if someone were to come into Veil and work Camila as a CI, they could take down a few small-time dealers. But small-time dealers weren't what Intelligence went after. And the thought vanished from Jay's mind just as quickly as it had popped up. 

Jay stood up and walked to the coffee machine. At this point, he was working off fumes and any little bit of caffeine he could consume helped. He was trying not to focus on how heavy his eyes were when he heard Hank walk into the break room.

You got your report?" Hank asked as soon as he entered. Jay turned to Hank and nodded yes. He pulled the report off the table and handed it to Hank. 

Jay stared at Hank as he read the report. He was hoping something on Hank's face would give away whatever he was thinking, but it didn't. Hank finished reading the report and looked up to Jay. Jay found himself struggling to maintain eye contact as Hank stared him down, waiting expectantly for an explanation.

"I was working her as a unwitting.". Jay finally said. "She works at Veil. A lot of drugs move through that place. She told me about the party. I saw an opportunity." He rattled off as nonchalantly as his nerves would allow. “But you're absolutely right. I should’ve put her on paper first.” Jay shook his head in disbelief at the mistake he had made. “I screwed up.”

Hank nodded in response to Jay. He continued staring at Jay, waiting for more. When it didn’t come, Hank asked what he was thinking.

“You sleeping with this girl?” Hank asked pointedly. Jay was relieved he was asked a question he didn’t have to lie about.

“No.” Jay said empathetically as he shook his head. The little details in between didn’t matter. It didn’t matter that he could have, or that he wanted too. In the end, he didn’t. And that was the only thing he had done right throughout this whole fiasco with Camila, so he clung to it. 

“Ok.” Hank said. He believed him, at least about the sleeping with Camila part. The rest, he wasn’t sure yet. “Document it, start working the case.” Hank said as he handed the report back to Jay. Jay looked back at Hank with a look of confusion at the order. “You’re already working the girl. May as well stay under. Figure out who murdered this girl. Right?”

Jay knew this was a bad idea. He knew he should come clean now about everything that happened. But he couldn’t. He dug himself too deep into this hole and he needed to pull himself out.

“Ok.” Jay answered. 

(Story Break)

Jay wanted nothing more than to go home and wash the memories of the previous night off him. He was going on over 24 hours without sleep and his body was starting to feel it. But digging himself out of this hole was more urgent than his need for sleep. After his conversation with Hank, he headed straight for Veil.

Jay entered the darkened bar and immediately made his way towards the bar where Camila was working. After a moment of small talk in front of customers, the bar was cleared leaving Jay and Camila the privacy they needed to talk.

“What the hell happened?” Camila asked concerned as she leaned into the counter towards Jay.

“The cops took me down to the station. Started drilling me with questions, like did I see anything. Did I know the girl that died.” Jay responded in a hushed voice.

Camila’s eyes widen at his response.

“She’s dead?” Camila asked in surprise. Jay nodded his confirmation. Camila shook her head and looked away.

“Did you know her name?” Jay asked a distracted Camila.

“Maggie. Don’t know her last name.” She managed to respond. Jay noticed Camila seemed to be lost in thought. 

“She was at the party right?” Jay asked.

Camila nodded softly in response.

“Did you see who she left with?”

Camila tilted her head and meet Jay's eyes with a look of disbelief that he was even asking her that question.

Jay was hoping he wouldn’t have to ask a lot of questions, but he realized quickly that wasn’t going to happen.

“Look, they were asking me if I saw-” 

“Ryan! I didn’t!” Camila interjected before Jay could finish. She stood up straight and shook her head to emphasize her point. “I didn’t watch her leave, ok?” 

“Ok.” Jay said. “I’m sorry.”

“I can’t believe she’s dead.” Camila said with a somber tone.

As Camila’s thoughts began to drift, Jay watched her for any signs that she was lying. She looked scared and concerned, not nervous or deceptive. He realized she may be thinking about her brother’s death, which was not too long ago. He looked down to the counter and saw Camila wrenching her hands together. He reached out and placed his hand over hers. Camila’s attention was instantly brought to their hands and she looked up to Jay.

“Are you ok?” He sincerely asked.

Camila smiled softly as she looked down at their intertwined hands. She squeezed Jay’s hand while answering.

“It’s always better when you are here.” Camila says.

Jay forced himself to smile through his mounting guilt.

**I hope you enjoyed! I hope to update again next week!**

**Notes for the Chapter:**

> I hope you enjoyed! I hope to update again next week!


	14. Chapter 14

**Notes for the Chapter:**

> I wanted to wait until Friday to post this, but I really loved this chapter and couldn’t wait for you guys to read it. I love reading the comments on here! Unfortunately, Jay is still spiraling but I hope you enjoy anyway! 

While Jay was trying to get more information on the victim from Camila, the rest of the team was busy trying to figure out Maggie's movements before her death. They pulled pods footage to retrace her steps and check if anyone was following her in the background. After they got an address, Hailey and Antonio went to check it out.

Upon entering, they noticed the apartment was not what one would expect from a junkie. It was nice, clean and had photos of the victim smiling happily with friends and family. A look through the mail further confused them. All mail was addressed to someone named Ella, not Maggie, which Jay had reported as the victim's name. The sudden arrival of an armed man in the apartment quickly brought them the answers they needed.

Maggie-as Camila knew her- was actually an undercover DEA agent named Ella. She had been trying to track down a drug supplier who was moving drugs through 5 clubs in the area. Just as Kim was relaying all the information they had obtained from the DEA's investigation, Jay was coming up the stairs. 

Jay glanced to the board and paled when he saw Alex, Camila’s friend’s, photo taped to the board. Hailey had noticed him coming up the stairs and the way the color drained from his face when he looked at the board. Hailey and Jay shared a moment of eye contact where Jay tried to act casual, but Hailey returned his gaze with a questioning look. She had seen the glint of recognition in his eyes from something on the board.

When Hank began to give orders to set up a buy with Alex, Jay realized he needed to jump in. 

“Uh, Sarge.” Jay hesitantly began. “I know Alex. I met him through Camila.” 

As other members of the unit gave each other looks, Hailey sighed and looked to the ground. It was starting to make sense why Jay was so nervous at the scene. There was more going on than a meet with a CI gone wrong.

Jay continued to make his pitch despite the way Hank was glaring at him.

“Let me work him. Make an undercover buy.” Jay finished as he waited for a decision.

Hank took a moment to think about Jay’s request. He knew Jay wasn’t telling him everything he needed to know. He could either call Jay out right now before this got any worse, or he could let him try to get himself out of the mess he was in. 

He decided on the latter.

“Ok.” Hank finally answered before adding, “you’re taking Upton.” 

“Alright.” Jay said. 

After the pair had left, Hank called Al into his office. 

“Kid’s hiding something.” Hank said as he sat at his desk. Al nodded in agreement. 

“Do me a favor. Run his muds and tolls. I wanna know what’s going on.” Hank asked Al.

(Story Break)

Tension wasn’t something Hailey was used to feeling around Jay, but on the drive to the Echo club, that’s all she felt. Hailey had questions she knew Jay didn’t want her to ask, and Jay had answers he knew Hailey wouldn’t want to hear. Unfortunately for both of them, going into an undercover buy wasn’t the right time for silence. They needed to figure out their stories and fact. As they turned into the Echo parking lot, Hailey knew she didn’t have too much time.

“So. How do you want to play this?” Hailey finally asked.

“Just let me do the talking.” Jay responded curtly. Hailey turned to face him when she picked up on his tone. She trusted him, enough to follow him into an undercover op blindly. But she also knew something about the case was making him nervous, and that made her nervous.

Hailey took a deep breath and braced herself to confront Jay.

“Jay.” She began calmly. “I need to know where your head is at.” Jay snapped his head in her direction at the comment. Hailey continued to speak softly, hoping to get through to Jay. “I’m good following your lead. I trust you; I’ve trusted you since the day I met you. If you say we are good, then I’ll believe you. But I need you to tell me.”

Jay watched Hailey’s eyes as they pleaded with him to be honest with her. He wanted to be, but he couldn’t bear the thought of disappointing her if she knew the truth. He looked away from her and down to her hand which was resting on the center console. He wanted to grab it and tell her everything. But he settled for just what he knew about Alex.

“I know Alex through Camila.” Jay looked away from Hailey as he continued to talk. “I know he deals. I’ve seen him sell at Veil, I’m pretty sure Camila buys from him.” Jay said in a defeated voice. “We are good, just follow my lead.” He added.

Hailey let out a sigh at Jay’s response. She knew there was more but decided not to push Jay. 

“We are talking about this after.” Hailey said firmly as she opened the truck and hopped out. 

“Copy that.” Jay said as he followed her lead.

When they walked into the club, they were able to find out Alex’s location from one of the bartenders. They walked up into the VIP section and found him standing by a balcony overlooking the club. 

“Alex.” Jay called out when he spotted the man.

“Ryan!” Alex exclaimed as he turned to greet Jay with a hug. Hailey tried not to let her thoughts wander at the way they greeted each other. _How well do they know each other_?

“This is my friend Hailey.” Jay said as he introduced her to Alex. 

“Nice to meet you.” Alex said as he reached out and shook her hand. Hailey, having spent a long time working undercover buys before her days in Robbery/Homicide, knew exactly how to play this.

“You too!” Hailey said happily as she flirtatiously smiled back to Alex.

“You only roll with pretty people, huh?” Alex asked Jay before turning back to Hailey. He returned her smile with a cheeky one of his own.

“Try to anyway.” Jay said as he looked at Hailey. It wasn’t lost on him how attractive Hailey was. Hailey couldn’t help but blush at Jay’s comment.

“Ask me, it’s a solid strategy.” Alex said with a chuckle. Jay felt himself tense as he watched Alex look Hailey up and down. “You two looking to party? Cause I’m feeling some pretty good vibes right now, especially from Hailey.” Alex said while quirking an eyebrow to Hailey. Jay’s jaw tensed as Hailey laughed at the comment.

“Sorry Alex, you’re not my type.” She responded with a flirty smile. 

“You’re welcome to try but, she’s taken.” Jay added casually to drive the point home. He hoped it would be enough to make Alex stop hitting on Hailey.

“I don’t judge Ryan.” Alex said as he pat Jay on the shoulder then looked back to Hailey. “Lets get some drinks. Yeah?”

“Yeah.” Hailey responded.

Hailey turned to walk and felt Alex place a hand on her back as he guided her to the bar. Jay noticed the movement and cleared his throat loudly to remind Alex he was still there.

“So, where’s your girlfriend?” Alex said while he turned to Jay. Hailey was taken back by the question but kept moving. 

“She’s working at Veil.” Jay answered casually. If Alex wanted to think he was dating Camila, Jay wasn’t going to correct him. It just made it easier to earn his trust. “I came by cause I wanted to see if you could hook me up.”

Alex stopped walking causing Jay and Hailey to do the same. Alex looked at Jay, confused at his comment.

“What do you mean?” Alex asked.

“I wanna buy some blow.” Jay responded casually. 

“Why are you asking me?” Alex asked, still confused about the conversation he was having. He glanced quickly to Hailey then back to Jay. 

“Because I know you.” Jay said with a chuckle hoping to ease any tension Alex might have.

Alex scoffed at the response.

“You know Camila better.” Alex said with an easy smile. When he noticed Jay stiffen at the comment, he instantly dropped his smile. 

“Oh um. She didn’t tell you?” Alex asked.

Jay felt himself getting irritated and shook his head.

“Tell me what.” Jay said as more of a statement than a question.

“She sells too and I’m guessing she’ll probably give you a better deal since your sleeping together.” Alex reasoned.

Hailey’s eyes darted toward Jay after Alex’s comment. She tried hard to keep herself composed and not show any signs of shock but internally, she was fuming.

“You know I would, but I don't like to mix business with pleasure.” Jay said in an effort to play off his surprise. “It makes things messy.”

“Business?” Alex asked as he looked at Hailey. She had quickly managed to get back into her flirty persona and smiled back to him. “So, this is more than just recreational?” Alex asked with a quirked eyebrow.

“Ya I’m looking to buy some big product. I got a lot of eager customers who want quality stuff.” Jay stated.

“We” Hailey interjected as she stepped closer to Jay and put her hand on his back. “have eager customers actually.” She said as she smiled up at Jay, hoping to remind him she was there. “We’re in this together.” She added. Jay cleared his throat and smiled at Hailey with a nod to let her know he got her message.

“How much you looking to get?” Alex curiously asked.

“Quarter key.” Jay responded. 

“I don’t have that kind of weight on me. I can get it. Meet here tomorrow at 1?” Alex asked. 

Jay and Hailey exchanged a look and nodded to each other. 

“Ok.” Jay said as he shook Alex’s hand. 

Having successfully arranged a buy, Jay and Hailey exited the club. Jay’s head was spinning from what Alex told him. How could he not notice Camila was selling? He spent time with her at her bar and at parties. He racked his brain for signs he may have missed as he walked intently to his truck.

Hailey was walking briskly behind him, trying to keep up with his pace. She was furious but didn’t want to call Jay out until they had put enough space between them and the club. After they got a block away, Hailey confronted Jay.

“Did you really know Camila was dealing?” Hailey asked in an irritated tone. 

Jay turned to look at her and then looked away.

“We are going to talk about this right now. Whether you want to or not.” Hailey said firmly. She was done trying to tip-toe around the subject. 

“No, I didn’t know but I’m not surprised.” Jay answered. “That’s why I was working her.” He added in defense.

Hailey stopped in her tracks. Jay had already lied to her in the truck, and she wasn’t going to let him lie to her again.

“You aren’t working her.” Hailey said incredulously. “You’re dating her!” She exclaimed with an unmistakable bite in her tone. “And you got her on paper now. You screwing her is a fireable offense. And now she’s mixed up in all of this?” Hailey firmly stated with zero effort to sugar coat the situation. “You’re lying to Voight, you lied to me. Are you gonna lie to the feds next?” 

Jay took a step towards Hailey and tried to keep his anger in check. 

“My relationship with Camila got us here.” Jay said defensively. He wasn’t sleeping with Camila, but if Alex thinking he had got them in the door, he was ok with it. “It got us the deal with Alex, who’s gonna lead us to the shooter.” He added.

"So you are sleeping with her." Hailey said in a matter of fact tone that she hoped masked her hurt.

Jay looked at Hailey and tried to find words to answer. He felt all the stress and exhaustion threatening to explode out of him. Instead of unleashing it on Hailey, he shook his head and walked away. 

“What are you doing?” Hailey said incredulously as she brought her hands up to run through her hair. She couldn’t believe how much trouble Jay had got himself into.

Jay turned quickly and took a few steps towards Hailey. He didn’t want to yell, so he took a deep breath and tried to collect himself.

“I’m fine. Alright. I’m fine.” He said firmly. “I can figure this out. Let’s let Alex take us to the supplier who might be good for the murder.” He reasoned. “In the meantime, I’ll talk to Camila and see what she knows.” He stood in front of Hailey and stared at her waiting for a response. He was doing it his way no matter what, but knowing she was on his side would make it easier.

Hailey shook her head and tried to clear her thoughts. There was no way out of this without Hank’s help.

“We gotta talk to Voight about this. He’ll know what to do.” Hailey said calmly.

“No.” Jay said adamantly. “Not yet.”

Hailey looked at him with exasperation. Jay knew he was losing her. He looked away and ran a hand through his hair. 

“I’m not sleeping with her. I just-I needed to help her. It’s my fault Luis is dead.” He said desperately to Hailey. “It was just supposed to be some help here and there. She started calling me to pick her up when she was too drunk or high to get home. That’s how I met Alex.” Jay said trying to explain what happened to Hailey. 

Hailey shook her head in disbelief. She couldn’t believe how skewed Jay’s judgement about the situation was.

“You didn’t just meet Alex, Jay. You didn’t just help Camila. You’re hanging out with them! They are your friends!” Hailey shouted back at him, unable to control her frustration any longer.

Jay shook his head at Hailey’s accusation. In all of this, never once had he considered any of these people his friends. Never had he thought he was doing anything other than paying off his guilt.

“Just give me a few hours. Please.” Jay said pleadingly to Hailey. He knew if Camila was mixed up in dealing, she had a good reason for it. He just needed some time to confront her and get the truth out of her. 

Hailey could feel in her gut that it was a bad idea, but she also trusted Jay. She knew he was in a bad place before he met Luis. She knew that bonded with Luis was a bad idea and would trigger something in Jay. She knew he was still struggling with Morgan’s death and his role in it. But she also knew Jay needed a win. He needed to fix this. And she wanted to give that to him. 

“A few hours. That’s it.” Hailey finally answered in a soft but firm tone. 

(Story Break)

After dropping Hailey off at the district, Jay headed straight to Camila’s apartment. To say he was upset would be an understatement, he was furious. How could he not have noticed Camila was selling drugs? Even though they weren’t dating, he spent a lot of his free time with her, either at work or at her apartment. He had seen drugs and paraphernalia around her place, but not enough to make him think she was selling. As he parked in front of her building, Jay took a few deep breaths to calm himself down. He needed Camila to tell him everything she knew about Maggie and that night at the warehouse.

Camila answered the door with a big smile on her face, the same way she always did. Jay struggled to return the smile but was able to muster one up. After inviting him in and offering some food, Camila realized Jay’s mood. He was leaning against a counter, arms crossed in front of him with a stern expression on his face. 

You ok?” Camila asked. When Ryan didn’t answer, she felt herself get nervous. “What’s wrong?”

“Look,” Jay began, “I’ve been talking to people. That woman who died Maggie, she was undercover DEA.” Jay said calmly with a hint of concern. He needed to sell Camila on the idea that he was on her side.

Camila’s eyes widen at the statement. She began to nervously look around the room as she processed his words. “I think she was working Veil too.” Jay added to make Camila more nervous.

Camila froze and looked back to Jay in shock. 

“She was DEA?” Camila asked in a low, scared voice. She sat at her table and ran her hands through her hair.

“Camila, what the hell is going on?” Jay exclaimed in an irritated voice. He quickly moved to the table and sat across from Camila.

“Nothing, nothing.” Camila said wide eyed as she tried to explain. “I just- after Luis died I couldn’t afford this place. I knew some people who were selling so I reached out. Just a little here and there just to make rent.” She said sheepishly. She took a deep breath as she tried to gauge Jay’s reaction. “I’m going to jail, aren’t I?” She sadly asked.

“No! Not for selling an 8 ball here or there. But if you know something about that woman-” Jay said in an effort to reassure Camila. Before he could finish, Camila had jumped to her feet and began to pace again.

“Of course, I don’t know anything about that!” She said incredulously. 

“Then why are you so worried right now!” Jay shot back.

“Cause she was a fed Ryan! OK!” Camila said in a panicked tone. “She was probably taking names.” She said as she began to look around the room. She continued to pace in the increasingly smaller room. “I need to get out of here.” She said firmly. She started to leave the kitchen when Jay stopped her.

“That’s not a good idea.” Jay said hoping to calm Camila down.

“It’s better than staying here, broke and scared!” Camila desperately responded to Jay. “I’ve been thinking about leaving town for a while. I haven’t because of you.” Camila explained as she looked up to Jay. All he could do was shake his head, he knew what was coming next. He tried to look away from her but Camila grabbed his face and turned him back to her. “I love you. Crazy as it is, I do.” She said as she looked hopefully into Jay’s eyes. 

Jay was speechless. He opened his mouth to speak but nothing came out. He felt terrible for putting Camila in this position, for leading her on, for making her fall in love with a person who didn’t exist.

Jay took her hands and softly pulled them away from his face. 

“I’m sorry Camila.” Jay was finally able to say. He shook his head softly and let go of her hands. He felt his breath hitch when he saw the tears fill her eyes as she nodded in understanding. 

“If you leave town, you will only make things worse. Please. Don’t leave.” Jay begged, knowing he had no right to ask. He felt an overwhelming pang of guilt when Camila nodded her head yes. 

**I was only able to write so many chapter because of the 4-day weekend that just passed. It will probably be a week until I can update again!**

**Notes for the Chapter:**

> I was only able to write so many chapter because of the 4-day weekend that just passed. It will probably be a week until I can update again!


	15. Chapter 15

**Notes for the Chapter:**

> Thank you for clicking in! Thank you to my beta Leigh0723 for all your help and helping me bounce ideas around. Also big thanks to my mutuals on tumblr for the support and exciting feedback! I hope you all enjoy!

After Hailey updated the unit on the details for the buy with Alex, the team quickly set up an operation to tail him. They were hoping Alex would lead them to his supplier at some point before the 1pm meeting, but that didn’t happen. Instead of leading them to his supplier as they hoped, Alex led them to an empty garage. Nonetheless, Intelligence was able to move in quickly and arrest Alex. Luckily, he was so surprised and scared, he opened up and told them everything he knew.

Sitting in an interrogation room, Alex explained how he knew Maggie, and what she was doing at the party. He earned an extra $1000 for making introductions of potential dealers to his recruiter. He had arranged this type of meeting for Maggie that night, with Camila.

Hailey and Jay were watching the interrogation from the observation room. When Alex named Camila as the person who was supposed to meet Maggie at the party, Hailey knew things were going to get a lot worse for Jay. After a sharp intake of breath at Alex’s information, Hailey looked to Jay. She could see the anger washing over his face as he leaned forward and rubbed his forehead. Hailey could hear Jay taking deep breaths as he if was trying to calm himself down. Just as Hailey took a step toward him, Jay seemed to be pulled from whatever thoughts he was lost in. He turned quickly and began to walk towards the door. Hailey, who was standing closer to the door than he was, quickly stepped in front of him with her hands out.

“Hey!” Hailey said firmly to get Jay’s attention. “You can’t talk to her. She’s a suspect now.” 

Jay looked at Hailey incredulously. He knew it looked bad, but Hailey didn’t know Camila like he did.

“No,” Jay said matching Hailey’s tone. “She is not. She would not do something like this.” He adamantly declared. “I know her. Just let me talk to her, maybe I can figure this out. I can get a name.” Jay desperately yelled at Hailey. He took a step to walk around her, but she quickly moved in front of him again and blocked his path to the door.

“Jay.” Hailey said firmly. When Jay continued to try to go around her, Hailey’s words became harsher. “No. Hey!” She shouted to get his attention. “You are not thinking straight! Whatever loyalty you have to this girl, whatever you two were, it is not worth it.” Hailey said in an attempt to reason with Jay. “You have to let it go, man.” She added, softer than her previous words had been said.

Jay could hear her words, but they weren’t registering for him. Camila needed him and he knew he could help her if he could just figure a way out. He owed it to Camila- to Luis- to try. Jay firmly shook his head and walked around Hailey to leave.

Jay made it all the way to the garage before he stopped to think about what he was doing. He knew Hailey was right, but she didn’t understand the whole picture. She didn’t understand Luis death was his fault. She didn’t understand Camila was broke and alone because of him. She didn’t understand Jay had no choice but to help Camila. He had to warn Camila.

Jay pulled out his phone and paused for a moment as he stared at it. He knew if he did this, made the call he was about to make, there was no telling what would happen to him. He took one more deep breath before shaking the doubt off and calling Camila.

“Do you have a bag packed?” Jay asked in a low voice as he exited the District garage. 

“No.” Camila responded with confusion and concern. "What the hell is going on?”

Jay ignored her question and began to give her instructions.

“Grab a bag. Take the L to Grant Park. No phone, no car, and I’ll meet you there.” Jay said as he got in his truck. 

(Story Break)

After Jay left the observation room, Hailey took a deep breath and tried to think of her next move. She tried reasoning with Jay, but he wasn’t thinking clearly. She thought about what Jay would do next. Although, she hoped she was wrong, she figured he was going off to warn Camila. She let out a deep sigh as she shook her head and quickly made her way back to the bull pen. Hailey grabbed her keys and jacket from the desk she was using and headed towards the stairs. She would figure out a plan as she was driving; right now, she needed to leave before Jay got too much of a head start.

Hailey had just begun her descent down the stairs when she heard Hank calling out to her. She turned and saw he was walking towards her while putting on his jacket. 

“Ride with me.” Hank said as he passed her and started down the stairs.

“Uh, I actually gotta-" Hailey attempted to say before being cut off.

“I know what you think you’re going to do Hailey.” Hank said as he opened the gate. He turned to look at her in the eyes. “Ride with me.” He ordered. Hailey swallowed hard and nodded.

In his truck, Hank was silent. She wasn’t sure where they were going, but Hank was tracking someone on his phone. She could tell from the route they were taking they were headed towards Grant Park. When she spotted Jay’s truck she realized why they were there. She inhaled shaprly as Hank drove around slowly while scanning the area. When he suddenly pulled over and parked, she knew he had spotted Jay. Hailey knew there was nothing she could say or do to help Jay, so she followed Hank in silence. She saw Jay walking into a tunnel, and realized they were heading to the opposite end.

Jay was running through his plan in his head when he approached the end of the tunnel. He was shocked when he was met with Hank and Hailey. 

“What the hell are you doing here.” Hank calmly asked Jay. He watched as Jay looked toward Hailey in anger. On her end, Hailey could feel the daggers Jay’s eyes were throwing at her.

“I don’t know what _she_ told you-” Jay began as he looked to Hank. The way Jay said she felt like a stab in the heart to Hailey. She steeled her emotions and returned Jay’s cold stare with one of her own. Before Jay could finish his thought, Hank had jumped in.

“You think she needed to tell me anything?” Hank said as Jay looked back to him. “Jay, you’re not that good.” Hank said in Hailey’s defense. “So, I’ll ask you again. What the hell are you doing here.” Hank asked again, more firmly than the first time. 

“I’m going to see Camila.” Jay said with conviction.

“I know that!” Hank responded incredulously. “I ran your muds and tolls. My question is why?” Hank asked with a tone of irritation.

“To see what she knows.” Jay said with a matter of fact tone. 

“Ok.” Hank said as Jay stared defiantly at him. “Well here’s what I know.” Hank began with a hint of sarcasm, “She’s a suspect in the murder of a DEA agent-”

"She didn’t kill anybody.” Jay interjected before Hank could finish. 

“You don’t know that.” Hailey added in a firm but calm tone. Jay glared at her in response then turned back to Hank. Hailey watched as Jay's chest moved up and down as he tried to control his breathing. 

“Here’s what you’re going to do.” Hank said as he pulled something out of his pocket. “You’re gonna work her. You’re gonna wear this wire. You’re gonna find out exactly what she knows and bury her ass. You understand me?” Hank ordered in a tone that left no room for argument.

Jay took several deep breath while he stared Hank down. He knew this was it. This was the moment where he had to choose, his life or Ryan’s. He looked away and nodded in understanding. He took the wire from Hank and walked around him to meet Camila.

(Story Break)

Jay was still trying to wrap his head around what was happening when he saw Camila standing on a bridge. He knew after being confronted by Hank, there was only one path he could possibly go down. As much as he wanted to warn Camila, he had a wire and knew Hank was listening. 

Camila was pacing on the bridge when Jay approached her. Upon seeing him, she ran towards him.

“I don’t understand.” Camila said in a panicked, hushed voice. “What’s going on?” She asked him with desperation in her eyes.

“Look, I talked to Mike,” Jay began, “He said Alex got busted and I should tell you.” Camila’s eyes widen at Jay’s statement.

“Alex?” Camila said in shock as she ran a hand over her face and began to pace again. “You’ve gotta be kidding me.”

Jay suddenly saw Camila in a different light. What he used to think was fear over being mixed up with the wrong people, he was now seeing for what it was: fear of getting caught.

“Cam, what is going on!” Jay harshly asked.

Camila began to cry and took several deep breaths.

“I lied ok!” Camila snapped back, still keeping her voice low. “I don’t just deal a little. I recruit dealers! I hook them up with product!” She finally revealed to Jay. 

“Ok, so you move drugs." Jay said in with an exasperated tone. “What does that have to do with the DEA agent?” He asked.

“I was recruiting her through Alex. Ok!” Camila’s voice began to rise the more truth she revealed to Jay. “That’s why she was at the party. She came there to talk to me.” 

“Did you? Did you talk?” Jay asked, hoping there was still a chance to prove Camila was innocent.

“No. I got nervous.” Camila answered calmly. “I heard someone call her a different name. Ella. I got nervous. I called it off. I told the guy I work for something was wrong and she wasn’t who she said she was.” 

“And then what?” Jay continued to press.

“Then she was dead.” Camila said matter of factly. 

“Who did you tell?” Jay asked calmly. He could feel they were finally at the end of this investigation. Camila just had to tell him the name, then they had their killer.

“No.” Camila said with a panicked voice. 

“Yes. You need to tell me!” Jay yelled. As desperate as Camila was to hide the name, Jay was equally as desperate to hear it. “You need to tell me the name so I can help you!” 

Camila paused momentarily and thought about telling the name. Unfortunately, fear won over.

“No.” Camila said firmly. “You can’t help me. No one can.” She said as she felt the panic boiling in her once again. “I need to get out of here. Are you coming with me? Yes or no?”

Jay felt like time stood still in that moment. Suddenly, listening to Camila’s story and being asked to run away with her, Jay realized how crazy it all was. How badly he had screwed up, how far he had fallen into the rabbit hole.

“Yeah.” Jay said hesitantly. He took a deep breath and tried to respond with more confidence. “Yeah, but first we gotta get out in front of this. The only way out of this for both of us, is to get proof you didn’t know he was going to kill her.”

For the first time since he met Camila, Jay told a lie he didn’t feel guilty about. He had mentally taken several steps back out of Ryan’s life and into Jay’s. He was once again an undercover cop working a CI. 

“He’ll kill me.” Camila said desperately. “He’ll kill us both.”

“No! I won’t let that happen.” Jay said. He could see he was losing her. She was ready to run and there was only one thing he could say to make her stay. He reached a hand out and held her face. “I think I’m falling in love with you.” Jay choked out in a strangled voice. This, he knew, was the worst of his lies; but it was the only way to get Camila to name the supplier.

Camila smiles through her tears as she finally heard the words she had dreamed to hear.

“Wallace Blake.” Camila finally said.

(Story Break)

Jay laid out a plan for Camila to set up a meet with Wallace at Veil. Since Hank and Hailey were listening in the wire, they were able to quickly send the unit into Veil to pose as customers. Once Hank got Jay’s signal over the wire, he would send the team in and arrest Wallace and Camila. All Jay had to do was play it cool and get Wallace to confess on tape.

This would prove to be a lot harder than Jay thought.

Wallace was immediately suspicious of Jay’s questions. The harder Jay pushed, the more weary Wallace became. Hank and Hailey listened in on the wire, feeling in their gut, Jay was pushing too hard. When they heard a scuffle ensue, Hank called off the mission and sent the unit in.

Intelligence stormed into the back room of Veil where Wallace and Jay were fighting. Jay had managed to knock the gun Wallace pulled out of his hands. By the time his team was shouting Chicago PD, Camila had picked up the gun and Jay had the upper hand on Wallace. 

Upon hearing the police shouting at her to drop the weapon, she instantly set it down and put her hands up in the air. As Hailey came around and cuffed her, she watched in relief as Wallace was also cuffed. Her relief quickly turned to confusion when rather than cuffing Ryan, the police where patting him on the back. She tried to make sense of the scene in front of her, was Ryan a snitch? Did he set her up? One look into his eyes, however, and she knew the truth.

Ryan was a cop.

(Story Break)

Jay returned to the District garage before anyone else did. He was grateful for the opportunity to clear his mind and prepare himself for many hard conversations he knew were coming. When he watched the black SUVs pulling in, he took one more deep breath as he walked out to greet them. 

One by one members of his team climbed out of the SUVs. Each one made eye contact, but quickly averted their eyes. They didn’t know Jay’s side of the story, but Camila had already begun to ask questions about who Ryan really was. It didn’t take long for the officers to start piecing together everything they knew. They were elite detectives and officers after all.

Hank exited the vehicle as Jay approached. 

“You’ve got 5 minutes.” Hank said to Jay before bringing Wallace in.

Jay braced himself to face Camila and opened the door. In the backseat of the SUV, Camila sat stone faced as she kept her eyes forward, refusing to look at Jay. Jay could see the puffiness in her eyes and knew she had been crying. When Jay failed to speak, Camila decide to.

“You’re really a cop.” Camila said in a cold, emotionless statement. Jay let out a sigh as he looked to the ground. He managed to look up at her to answer.

“Ya.” Jay said with pain in his eyes as he looked at the woman he had been lying to for weeks. “I don’t know what to-” Jay’s apology was cut off by an angry voice.

“You make me sick.” Camila harshly said with disgust in her voice. “Get the hell away from me.” She shouted at him as she finally met his eyes. 

Jay looked to the ground and nodded softly. As Antonio came around to escort Camila into the District, Jay took a step back to give them space. He tried to quiet his racing thoughts as he began to walk, only to freeze when his eyes met Hailey’s. 

Jay realized this was the first time he was actually seeing Hailey with a clear head since the case started. His mind had been so clouded by guilt and focused on saving Camila that he never saw what it was doing to Hailey. He cringed at the disappointment on her face and her red rimmed eyes that were coldly staring back at him. Remembering the way he had spoken to her in the tunnel, Jay understood why. 

Hailey took a few deep breaths as she tried to think of what to say, what to do. In the end, all she could do was shake her head and walk away. Jay watched as Hailey looked to the floor and walked away, shoulders slumped, and head hung low. 

(Story Break)

Hank and Al weren’t surprised to hear Wallace say he had nothing to do with Maggie’s murder. He attempted to sell a story which put the murder on Camila, claiming she got scared when she heard someone call Maggie by a different name. Hailey, who had been watching from the other side of the mirror, took the accusation as her cue to enter the interview room with Camila. 

Antonio had already started interviewing Camila when Hailey entered the room. She stood off to the side, listening as Camila told Antonio the same story she had told Jay. She set up a meet for Maggie and her supplier, got nervous when she heard someone call Maggie by a different name, and told Wallace she thought Maggie was a cop.

“Wallace says you’re the one who shot Maggie.” Hailey said once Camila finished telling her story.

“He’s lying.” Camila said desperately. 

“That’s not good enough.” Antonio said firmly. “Where were you when she was murdered.”

“You know what.” Camila said as she leaned forward. “When she was getting murdered, I was in the back room screwing your partner.” She spit out at Antonio. 

Hailey and Antonio exchange knowing looks to each other. Hailey nods and leaves the room as Antonio followed behind her. 

“We gotta confirm her alibi.” Antonio says in an irritated, hushed voice. He had hoped they’d be able to keep Jay out of the reports, but if Camila was using him as an alibi, it wouldn’t be possible. Hailey nodded as she stared off in the distance. “You wanna do it?” He finally asked.

Hailey took a deep breath and nodded. 

(Story Break)

Hailey steadied her nerves as she prepared to have an uncomfortable conversation with Jay. She walked into the bullpen and looked around for him. Upon seeing her, Kim motioned towards the breakroom where Hailey could see Jay sitting with his head in his hands. She nodded her thanks to Kim and walked toward the breakroom.

Jay stood up when he heard Hailey walk into the room. He had not been able to stop thinking about how he’d treated her the past few days since they returned to the District. 

“Hailey I am-” Jay began.

“I need to verify Camila’s alibi.” Hailey curtly said, completely ignoring Jay’s attempt at an apology. Jay nodded in understanding and sat back down. 

“What happened that night.” Hailey asked firmly as she crossed her arms over her chest. 

"Uh. We were hanging out. Around 2:30am I decided to leave. Camila said she’d come with me.” Jay paused remembering what happened next. He looked up to Hailey who was staring at him with a stern look on her face. He swallowed hard and continued. “She said she needed to show me something in a backroom.” He said before looking away. He did not want to see Hailey’s face for the next part. “When we got there, she started kissing me. We-uh-made out for a minute then stopped.” He paused when he heard Hailey inhale sharply. “I told her I was leaving. On the way out, we bumped into Maggie. She wanted to talk to Camila. I wanted to leave. Camila asked for a couple of minutes to say bye. I went outside and waited for her.” He finally finished.

Hailey looked on as she took a few deep, calming breaths before she spoke.

“The last time you saw Camila was inside with Maggie?” Hailey coldly asked.

“Ya. Camila was walking back towards her friends and Maggie was following her.” Hailey nodded then turned to leave. Before she got out the door, she paused when she heard Jay call her name.

“Hailey.” Jay said in a low, almost whispered voice. “I never had sex with her.” He added desperately, unsure of why it even mattered. He didn’t care what Camila said or what went into the reports. He just needed Hailey to know he was telling the truth about how far he went with Camila. 

Hailey, without acknowledging his statement, walked out.

(Story Break)

After leaving the breakroom, Hailey walked straight towards the interrogation room. She opened the door and quickly entered the room, closing the door loudly behind her.

“Your alibi doesn’t hold up.” Hailey said coldly with her arms crossed in front of her chest. Camila was caught off guard. 

“If Ryan is saying he wasn’t with me, he is lying.” Camila said with a scoff.

“The _detective_ ” Hailey corrected “is saying he saw Maggie _after_ the backroom. Last time he saw her, she was following you as he left the warehouse.” Hailey said with a calm but stern voice. 

Camila swallows hard and looked away from Hailey.

“I’m not saying anything else without an attorney.” Camila finally said. 

**Notes for the Chapter:**

> I hope you enjoyed! I hope to update again in a week or 2! 


	16. Chapter 16

**Notes for the Chapter:**

> Thank you all for reading and for all the feedback! This chapter will wrap up the 5-7 to 5-10 arc from the show! 

Hank was in his office doing paperwork when he got a call from the DEA informing him they were taking over the case. He knew it was coming, but he had hoped to have more time. He knew the DEA was out for blood since one of their own was killed and would go after Camila just as hard as Wallace for the death. Hank feared Camila would use her relationship with Jay as a bargaining chip. He asked the DEA for a couple of hours to tie up some loose ends.

They gave him one.

“Halstead.” Hank said as he called out from his office. “In here, please.” 

Jay cleared his throat and tried to push down all his nerves. He rose steadily and made his way into the office, shutting the door behind him instinctively. 

Hank stared Jay down as he sat down and began to speak.

“Look Hank. I’m sorry. I know I screwed up.” Jay said, looking his Sergeant in the eyes. “You have my word; I am committed to making this right. Whatever it takes.” 

Hank shook his head at Jay’s statements and stood up. He leaned against a wall and put his hands in his pocket.

“Your word doesn’t mean that much right now, Jay.” Hank bluntly stated. Jay felt the panic rising in his throat as he continued to listen. “You lied. Right to my face, multiple times. You put this unit _, my unit_ ,” Hank added with emphasis “at risk.” Hank shouted.

Jay nodded in understanding as he broke eye contact, unable to hide the shame and guilt he was feeling. 

“I’ve set up an appointment for you with a psychologist.” Jay’s eyes shot up at Hank’s comment. “Someone I trust.” Hank added. 

“Sarge, I-” Jay’s protest was cut off by Hank.

“I hope you can dig yourself out of this hole Jay.” Hank said sincerely. “I really do. Until then, you’re on desk duty.” He added as he walked to his door and opened it, motioning for Jay to leave. 

(Story Break)

After Camila asked for a lawyer, an officer took her to booking then down to a holding cell. Hailey, meanwhile, busied herself with reports. She was at Trudy’s desk filling out the paperwork when they saw a group of DEA agents heading up to the bullpen. She shook her head irritated as she turned to Trudy.

“So that’s it, then. We do all the work; feds swoop in for the credit.” Hailey said harshly.

“That’s how it goes.” Trudy said with a smirk. “But that’s not what you are worried about.” She added as she shuffled papers on her desk. Hailey looked up to her and took a deep breath. 

“You did everything you could Hailey.” Trudy said in a sympathetic tone. “Jay was over his skis on this one.” 

Hailey nodded as she thought about Trudy’s words. She did everything she could to stop Jay from making things worse. Now, with the feds involved and with Camila using Jay as her alibi, the situation was out of their hands.

“What do you think will happen?” Hailey sadly asked Trudy, already knowing the answer.

Trudy let out a deep sigh before answering.

“Depends on how pissed Camila is.” Trudy stated. Hailey nodded in agreement then looked back to the stairs. 

“Do me a favor?” Hailey asked as she turned back to Trudy. “Can you stall the feds?” 

Trudy grinned in response as Hailey made her way to the holding cells, stopping when she arrived at Camila’s. Hailey could read the fear and anger all over Camila’s face. She hoped she wasn’t too far gone to reason with.

"What’s his real name?” Camila asked sadly, not looking away from the spot on the wall she had been staring at. 

“It doesn’t matter.” Hailey coldly responded. Camila looked over to her with a pleading look in her eyes. Hailey found herself feeling sorry for Camila and answered. “Jay.”

Camila nodded at Hailey’s response. She turned back to the spot on the wall and resumed staring at it. 

“Wallace confessed.” Hailey said in a soft but firm voice. “DEA is taking over. They are looking to make an example out of everyone involved.” Camila turned to look at Hailey with fear in her eyes. “Wallace is going down for murder. You got lucky there, but they are looking to charge you with felony drug distribution and accessory to murder.” Hailey added.

Camila nodded in understanding; she knew what was happening.

“I can help you.” Hailey said softly. “I can talk to the DEA, convince them you were working with us all along. That you are a CI for the Chicago PD and led us to Wallace.” Hailey said slowly. When Camila looked over to her, the fear in her eyes had been replaced with anger.

“As long as I leave Ryan out of it? Say I didn’t know him?” Camila spitefully asked.

“You didn’t know him.” Hailey curtly said. She took a deep breath and tried to watch her tone as she reasoned with Camila. “Detective Halstead recruited you as a CI. Every interaction you had with him, every party he picked you up from, every night he spent at Veil, all of it was in the capacity of a CI with your handler.” Hailey took a step towards the cell. “There was no friendship. No making out in a backroom.”

“So you want me to lie.” Camila said in a defeated voice.

“I want you to give yourself a second chance. Make these charges go away, give yourself a shot at a life. We can get the DEA to back off on your charges.” Hailey said.

Camila knew she was backed into a corner. She had made a lot of mistakes that could go away easily simply by changing one little detail in her story.

“Ok.” Camila said. Hailey looked at her expectantly, wanting to hear her say it. “I was working as a CI for Detective Halstead. There was no friendship. No relationship.” She said sadly. 

Hailey watched as Camila’s shoulders dropped under the weight of the pressure. 

“You’re doing the right thing.” Hailey said, not sure if she was trying to convince Camila or herself. “You’ll get a second chance. You can do it right this time.” Hailey said as she left the holding cells. 

Hailey made her way up to the Intelligence bullpen just as the DEA were leaving to interview Wallace. She stepped aside for them to pass through then motioned for Hank to follow her. Hailey, followed by Hank, walked over to Al’s desk and told them about Camila’s story.

“I talked to Camila.” Hailey began. Hank and Al quirked an eyebrow at each other then looked back to Hailey.

“I called her out on her alibi. She lied about being with Jay when Ella was killed. After that, she changed her story. Said she’d was working as a CI for Jay. Panicked when she found out Wallace had killed a DEA agent. She thought she use Jay to leverage us for a good deal but realized the truth was a better way to go.” Hailey rattled off the Hank and Al. 

Al nodded in understanding at what Hailey was saying. 

“Sounds like she came to her senses.” Al said as he looked over to Hank. 

Hank was still watching Hailey, trying to think of his response. He knew the new version of the story could get Hailey into a lot of trouble if anyone ever found out. He wasn’t sure if he wanted her to carry the burden. 

“Write it up. I’ll let the DEA know.” Hank finally said. He reached out and gave Hailey’s shoulder a squeeze in recognition of what she had done. Hailey made her way to her desk and began writing up Camila’s new statement. The more she wrote, the more frustrated she began to feel over the entire situation. She had tried to be there for Jay, tried to encourage him to talk to someone, but instead he just kept digging himself deeper and deeper into a hole. She finished signing some papers and walked them into Hank’s office. 

After dropping the paperwork on Hank's desk her anger and need to confront Jay led her to Trudy’s desk and without hesitation, when Hailey asked for Jay's home address, Trudy told her. Hailey missed the smirk on Trudy's face as she turned around. Trudy knew Jay was in for it.

(Story Break)

Jay was relieved to finally be home after the stressful week he had. Even though his body was physically exhausted, his brain was running at 100 miles per hour. How badly had he screwed up? How much trouble was he in? How much damage did he do to his friendship with Hailey? Hoping to push all the questions aside, he headed into the bathroom to take a shower. 

A few minutes later, Jay felt refreshed as he got dressed and made his way to the kitchen. He had just grabbed a beer from the fridge when he heard a knock at the door. When his initial attempt to ignore the door was met with a louder knock, he sighed and made his way to open it. 

Jay was surprised to see his partner standing on the other side.

“Al.” Jay said with confusion. 

“Hey kid.” Al said as Jay stood in the doorway. When he didn’t move, Al brushed past him and entered the apartment. Jay dropped his head, knowing if Al was there, it was to deliver bad news. Al walked around the apartment, scanning all the surfaces for something you shouldn’t find in a cop’s home. 

“What are you doing?” Jay asked when Al made his way into the bedroom. Al continued to walk through, not touching anything but searching nonetheless.

“Has Camila ever been here?” Al asked as he entered the bathroom and opened the medicine cabinet. When he started picking up bottles and reading the labels, Jay realized what was happening. 

“Are you looking for drugs?” Jay asked incredulously. Al didn’t respond as he walked past Jay.

“Answer the question.” Al said in a very calm voice. Jay let out a huff as he shook his head.

“No. She’s never been here.” Jay said firmly. “And I don’t do drugs. Never have, never will.” He adamantly stated. 

Al walked into the main living area, closely followed by Jay. He entered the kitchen and leaned against a wall, putting his hands in his pockets. 

“Feds are taking over.” Al said matter of factly. Jay’s eyes widen at the statement. He ran a hand over his face, suddenly nervous about what would happen to him.

“How bad is it?” Jay asked in a defeated voice.

Al quirked his eyebrows at the question.

“Camila changed her story.” Al said nonchalantly. “Upton called her out on her alibi, reminded her that an undercover detective saw Maggie with her 15 minutes before she died.” He paused when he heard Jay let out a breath of relief. “Realized leveraging an undercover detective for a deal wasn’t the best play.”

Jay looked at Al in shock, not quite understanding what he said.

“Upton is writing up a new statement. Feds are going to go easy on Camila, since she was working as your CI.” Al added. Jay shook his head understanding. He couldn’t believe how stupid he had been, and how lucky he got. 

Before Jay could respond, there was another knock at the door. Both Jay and Al turned towards the door then back to each other. Jay wasn’t expecting anyone, but he was grateful for the interruption. He looked to Al expectantly, hoping Al would excuse himself. Instead, Al took off his jacket and walked around to his couch, sitting down comfortably. He had no intention on leaving until he knew Jay understood the gravity of his situation.

Jay shook his head and ran a hand across the back of his neck as he walked to his door.

Hailey had worked herself up on her drive to Jay’s apartment. By the time she knocked on the door she had already gone through 5 different conversations with Jay in her head. She made the short walk up the stairs to his apartment and braced herself to confront Jay. She forgot everything she had planned to say as soon as he opened the door.

“Hailey?” Jay said in surprise as he put his hands in his pockets. Hailey waved him off when he stepped aside to let her in. Jay nodded in understanding and leaned against the doorway as he looked back to Hailey, waiting for her to speak. When she didn’t, he took the opportunity to attempt an apology.

“Hailey,” he began, not entirely sure what he was going to say. “You’re probably tired of hearing apologies from me.” Jay almost whispered as he continued to think about what he wanted to say. Hailey’s eyes narrowed at Jay’s statement. Before he could continue, Hailey interjected.

“What I am tired of Jay, is you acting like everything is fine when you know it isn’t.” Hailey said sharply. Jay was taken back by her comment. 

“I know I lost focus on this case,” Jay started, “and the only reason I’m not facing disciplinary action is because you cleaned up my mess. But I want you to know-”

“All I want to know is that you're going to get help.” Hailey interjected firmly. She paused when Jay furrowed his eyebrows at her. “Not a distraction; not a temporary solution. _Real help_. I want to see you making real changes in how you deal with problems.” She said, feeling her breath hitch. She felt her voice getting louder as she continued. “Because I'm not hanging around to watch you self-destruct. And if you keep dealing with things the way you have been, keep running away from your problems, that's exactly what's going to happen.” Hailey added with a bite in her tone. 

Jay looked at the floor, unable to handle the disappointment in Hailey’s eyes. Hailey waited, hoping to hear Jay say something to let her know he heard her. When all he could do was shake his head, she knew she had her answer. Hailey sadly looked down and nodded as she let out a big sigh. She began to walk away but stopped herself, needing to make herself clear.

“Seriously Jay. Get help with your problems, or don’t bother calling me.” 

Before Jay could answer, Hailey was walking down the hallway. Jay was left in the doorway, stunned. No one had ever issued him an ultimatum to get help. Usually, people let him deal with his issues on his own, waiting for him to come to them. This made it easy for Jay to push aside his problems and sweep them under the rug. Hailey, instead, had called him out every time. Despite being lied to repeatedly, despite the way he had treated her, Hailey never gave up on him. Even now, when she was ready to walk away from their friendship, she was giving him another chance. 

Jay suddenly felt a hand clap on his back. He turned to see Al, sliding an arm into his jacket as he was walking out the door. Al had originally planned to talk to Jay about therapy, but no longer felt the need to. Hailey had said all that needed to be said. 

“You got lucky with Upton covering for you. You might not get another chance like that.” Al said as he adjusted his jacket. “We all need someone to call us out on our bullshit. You’ve had 3 people do it tonight.” He added as he looked Jay in the eyes. “The rest is on you.”

Jay stood in place as he thought about the past few months. Erin leaving, Morgan and Luis’s deaths, all the lies, all the bad decisions. Jay realized he was at a fork in the road and had two choices. Continue trying to ignore the problem or get help. 

**Notes for the Chapter:**

> I hope you enjoyed! I hope to update again in a week or two. 


	17. Chapter 17

**Notes for the Chapter:**

> Hello everyone! Thanks for reading and commenting! Thank you to my beta Leigh0723 for all your help!

Chapter 17

Over the next few weeks, Jay put more focus on his mental health. Even though the first appointment didn’t go well, he barely spoke during the whole 50 minutes, but he was determined to put in the work and get better. Hailey’s words kept repeating in his head. _Get help with your problems, or don’t bother calling me_. It never occurred to him to cut his loses and say goodbye to Hailey. It would’ve been easy; it’s not like they really worked together on a daily basis. But something about how Hailey had stood by him for weeks as he repeatedly pushed her away made him want to put in an effort.

Once Jay began to open up more to therapy, he became more open to the services VA centers offered. He started going to a support group for veterans with PTSD at his local center. He found it beneficial not just to talk openly about what he experienced on his tour but also to help other who struggled. As the days went on, Jay began feeling more and more like himself, which did not go unnoticed by the rest of the team. They were grateful when he started accepting invitations to Molly’s and get togethers outside of work.

Jay hadn’t heard from Hailey since the night she showed up at his apartment. Jay wasn’t sure if she had decided he wasn’t worth the effort, or if she was waiting for him to call first. There were a few times that first week where he would type out messages to her only to end up deleting them. _I want to see you making real changes in how you deal with your problems_. He knew the changes she was talking about couldn’t happen in a week, so he waited until he could show her that he took her words to heart.

Even though Hailey didn’t reach out to Jay during those weeks, he was often on her mind. She worried at first that her words did more harm than good, but she couldn’t bring herself to call him. After the first week, not knowing how Jay was started to eat away at her. That’s why, one day while volunteering in the Community Play garden, Hailey found the strength to ask Trudy about him.

“How’s Halstead doing?” Hailey asked as she was pulling weeds along side Trudy. She had hoped she asked casually enough for Trudy not to read too much into it. 

“Seems to be firing on all cylinders.” Trudy nonchalantly answered with a quirked eyebrow. Hailey let out a sigh, knowing Trudy was purposely being vague. She straightened out and brushed some dirt off her thighs before looking back to Trudy with expectant look.

“You could just call him and ask.” Trudy said in response to Hailey’s body language. 

“No, I can’t.” Hailey said with a defeated tone. She ran a hand across her forehead as she remembered her words from that night. She had given him an ultimatum, and it seemed like he made his choice. 

“I can tell you that he hasn’t been in the best of moods on desk duty.” Trudy said as she bent over to resume pulling weeds. “But he’s doing what he needs to prove to Voight that he belongs in Intelligence.” She added. 

Hailey softly smiled at the information. She hoped Jay wanting to stay in Intelligence was enough motivation for him to get help. 

After that weekend, Trudy began randomly sharing bits of unsolicited information about Jay to Hailey. She casually mentioned her week went a lot smoother without the cranky detective looming around the district doing paperwork. Voight had seen enough positive change to let Jay return to the field, something that made Hailey very happy. Another time, Trudy mentioned she had resumed calling Jay by his nickname chuckles, due to the return of his sense of humor. 

With each week, the tiny hints into Jay’s progress brought both happiness and sadness to Hailey. While she was happy he seemed to have dug himself out of the hole he was in, it hurt that she still hadn’t heard from him. Nonetheless, she was beyond grateful that Trudy continued to keep her updated without making her feel like she had to dig for information. 

One morning, Hailey was reading a file while standing in line at a coffee shop by Area Central. Even though she was focused on what she was reading, she couldn’t help but notice 2 familiar voices having a conversation behind her.

“All I’m saying is the ladies love a man who can sing.” She turned to see familiar faces standing 1 person away from her in line. “This karaoke machine is going to open up a lot of opportunities-”

“Unless you can’t sing! Then the only opportunities it opens is for you to make an ass of yourself.” Hailey chuckled as she motioned for the man behind her to go in front of her. 

“Hey guys!” Hailey said as she interrupted the conversation. Adam and Kevin, completely surprised, turned to her and each greeted her with a hug. “What are you two doing up here?” She asked.

“We gotta run up to Area Central to pick up some paperwork.” Kevin said. “I’m glad we ran into you though. You coming to Molly’s on Friday for Platt’s birthday?” 

“Mmhm,” Hailey said as she scrunched her face. “I don’t know. Karaoke machines attract the wrong crowd.” Adam laughed as Kevin threw his head back in feigned exasperation. 

“I’ve been trying to tell him.” Adam said, shaking his head. “Liquid courage is going to make a lot of misguided souls think they can sing a lot better than they do.”

“And I’m trying to tell you,” Kevin said, putting an emphasis on the ‘I’m’, “since I can sing, this is not something I need to worry about.” 

“Ya, I am definitely in the liquid courage leads to bad decisions category.” Hailey joked. “But I will probably stop by nonetheless. Platt mentioned her annual tradition of buying Malort shots for the team, so I may pop in for that."

“See!” Adam said as he clapped his hands together. “Platt, shots and karaoke. Who could turn that down?” He cheekily said to Hailey. 

Hailey laughed as she thought about the invitation. When Trudy had asked her, she had politely turned it down. The last thing she wanted to do was intrude on a team gathering, especially since she didn’t know where she stood with Jay. But, the more she thought about it, the more she felt like a night out is just what she needed. 

“Alright, but if I end up singing, I want a duet.” Hailey pointedly said to Kevin, who reached out a hand to shake on it. 

“So we will see you Friday?” Adam asked with a cheeky grin.

“I will be there.” 

(Story Break)

As the members of Intelligence began to finish up their paperwork, they began discussing their plans for the evening. They were all excited to be out as a group with other first responders, something that hadn’t happened for a while. They were even more excited, however, about the free shots of Marlot they knew Platt would be buying. 

Once they were packed up and ready to head out the door, Adam sent off a quick text to Hailey letting her know they were on the way. Hailey, who had made sure to leave work at exactly 5 to give herself time to get ready, responded quickly.

“Ok, Hailey will meet us there in 10. Let’s go!” Adam said as he put his phone back in his pocket and grabbed his jacket. Jay’s head instantly turned at the sound of Hailey's name.

“Hailey?” Jay asked.

“Ya. We saw her the other day. She is coming.” Kevin added as he followed Adam down the stairs. 

Jay nodded casually as he felt his heart beating in his ears. He wasn’t at all upset to hear she was going, but he was suddenly nervous. He hadn’t seen or spoken to Hailey for weeks. The last time they saw each other, he was at an all-time low point in his life and had made a huge mess of a case. To make matters worse, Hailey had been the one to cover for him and clean up his mess despite the constant lies he told her and the way he treated her. 

Even though Jay knew he was in a better head space now than the last time he saw Hailey, he still wasn’t entirely sure Hailey wanted anything to do with him. He took a deep breath and headed down the stairs, determined to give Hailey more time.

“Hey Trudy.” Jay said as he approached the desk. “I’m really sorry but I can’t make it tonight.”

Trudy stopped what she was doing and looked Jay in the eyes. 

“Why’s that.” Trudy asked in a matter of fact tone.

“I just got a call from Will. I gotta help him out with something.” Jay explained.

“Good!” Trudy said with a big smile. “I was worried it was because Upton was going tonight.” She said as she grabbed her keys and began to walk out of the building. “Because if that’s why, I would’ve had to give you a speech about how you have nothing to worry about because Hailey would want to see you.” She said looking back at Jay who was following her. “Then if Hailey asked where you were, I’d have to tell her ‘avoiding you’.” Jay looked at her with a stunned expression on her face.

“And we all know I _hate_ being caught in the middle of other people’s drama.” Trudy added. 

Jay nodded as he took in Trudy’s words. Would Hailey really want to see him? 

“Maybe I can convince Will to tag along to Molly’s.” Jay said casually as Trudy got into her car.

“Maybe.” Trudy said with a knowing smirk. “See ya in a few, Halstead.”

(Story Break)

Hailey couldn’t remember the last time she felt nervous about meeting friends in a bar, yet this is where she found herself as she exited her Uber in front of Molly’s. She could see Intelligence and members of Station 51 through the window gathering at the bar and passing shot glasses around. She took one more deep breath, and opened the door. 

“Upton!” Kim yelled as she saw Hailey enter. At the sound of her name, Jay felt his chest tighten in anticipation as he turned towards the door. 

Jay found himself at a loss for words as he took in Hailey’s appearance. She was dressed casually, wearing a tight pair of jeans and loose-fitting shirt that hung off one of her shoulders, revealing the straps to her tank top underneath. Jay had only ever seen her in work attire and was suddenly realizing how attracted he was to her. Just as he was about to set his shot glass down, he heard Adam. 

“Hold up! Hold up!” Adam said as he held his hands up for everyone to wait and made his way to Hailey.

“Just in time!” Adam said enthusiastically as he bent down to give Hailey a hug. Hailey blushed at the gesture as Adam handed her his shot glass and guided her towards the bar with a hand on his back. 

Jay watched the scene unfold with furrowed eyebrows as he tried to figure out when Adam and Hailey became friends. Before he could spend too much time on this mystery, he felt a nudge on his shoulder. He looked up to see Will staring at him with a questioning look on his face. Jay cleared his throat and shrugged off Will’s questioning look with a faint head shake. 

Adam ordered himself another shot of Malort as Hailey made her way to the bar, eyes meeting Jays. Still not sure of where she stood with Jay, she nodded a greeting in his direction. Jay responded with a warm smile and nod. Will, sensing the tension coming off his brother, decided to step in and move things along.

“Alright guys,” Will said as he raised his shot glass, “let’s try this again. To Trudy.” He said as he nodded at Trudy.

“To Trudy!” The group said in unison as they downed their shots. 

(Story Break)

After getting new drinks, the group began to disperse. Despite her initial hesitation, Trudy ended up being the first person to sign up for karaoke. As she began flipping through her song choices, the members of 51 began to take their seats at tables, anxiously awaiting her performance. Some remained seated at the bar and a few made their way to the pool tables. Antonio and Adam had been bantering about pool since they arrived and had decided on a quick game to settle the argument. Kim and Hailey found themselves bouncing between the karaoke machine, the bar and the pool tables. After about an hour, Hailey found herself throwing her name into the hat after listening to Adam and Antonio going on and on about who was the better pool player. 

Jay, who had remained in his seat at the bar since he arrived, kept finding himself looking back towards the pool tables at the sound of Hailey’s laughter. He couldn’t help but feel a sting of irritation every time he saw Adam flirting with Hailey. It wasn’t the flirting that bothered him, it was that Adam noticed Hailey before he did. Despite having been in each other’s orbit for the last 6 months, Jay had somehow never noticed how attracted he was to Hailey. He had spent lots of time with her on the job and outside of work, yet he couldn’t think of a single time when the conversation took a flirty turn. 

Watching Adam and Hailey, whom he didn’t even know were friends, hanging out together was making him jealous. He took another swig of his beer and tried to refocus his attention on the conversation happening at the bar. Will had noticed the way Jay kept looking back towards Hailey and decided to call him out on it. 

“So,” Will began, , “what's up with you and Hailey?” He said bluntly as he leaned against the bar top **.**

Jay quirked his eyebrow at his brother as he lifted his beer to his mouth.

“Not sure what you mean.” Jay answered with the faintest hint of sarcasm.

“Well,” Will began, shifting on his stool, “you haven't spoken to her since she came in and it seems like you are trying really hard not to move from this spot even though your attention is clearly at the pool table.” 

“It's nothing.” Jay answered with a sigh. 

“Which means you did something.” Will pointedly responded with a firm nod.

Jay shook his head at his brother and took a deep breath.

“You know that case I got caught up in a few weeks back?” Jay asked. When Will nodded in response, he continued. “She was partnered up with me for it.” Will’s eyes widened at the revelation. “When it started to go bad, instead of coming clean, I lied to her. Over and over. And I treated her like shit.” Jay said pointedly. “And despite that, when she found out, she covered for me so I wouldn't get in trouble. She put her career on the line to cover for me.”

“Ok,” Will said trying to follow along. “So, she’s upset you lied to her and acted like an asshole?”

Jay scoffed at the question.

“I wish it was that simple.” Jay said as he ran a hand down his face. He leaned forward and set his elbows down on the counter. “She came to my place that night. Told me to get my shit together and get help or lose her number.”

“I like her.” Will said, earning a chuckle from Jay. 

“Ya. Me too.” Jay said with a smile that made Will question whether he meant as a friend or something more. 

“So, Hailey is the reason why you’ve been taking therapy seriously these past weeks.” Will asked. 

Jay swallowed hard and nodded his head. 

“I don’t want to let her down.” Jay said as he looked at his brother. Will noted the desperation in his eyes. “I haven’t seen or talked to her since that night. I just want to make sure I've got my head on straight before I reach out.”

Will let out a deep sigh at all the information Jay had shared with him. He knew the basic details about Camila and Jay almost losing his job, but he had no idea Hailey was involved. Jay had left out the part about being partnered with her. Normally he would be surprised Jay left out such an important detail, but after hearing about the lies and the confrontation he had with Hailey, he understood why. He could see regret on Jay’s face as he talked about lying to Hailey and how she covered for him. Will was proud of Jay for taking therapy seriously and he felt like he had Hailey to thank for it. As he watched Hailey and Adam walking to the end of the bar together, he realized Hailey was good for Jay in a way no one else had been. 

“Well brother,” Will said as he pushed himself away from the counter, “if I were you, I wouldn't wait too long.”

“Oh ya?” Jay said with a quirked eyebrow. “Why's that?”

Will let out a sighed as he looked over his shoulder to the other end of the bar. He laid a hand on Jay’s shoulder and gave it a firm squeeze. 

“I don’t think you’re the only member of Intelligence interested in Hailey.” Will said as he motioned to the other end of the bar.

When Jay’s eyes followed Will’s gaze, he saw Hailey leaning against the bar looking through the karaoke list. Standing close behind her was Adam who was looking over her shoulder. He watched as Adam pointed to the list and leaned in to say something in Hailey’s ear. Whatever it was made Hailey erupt into laughter as she spun around and gave Adam a high five. Adam pulled her in for a hug and moved his arm to her back as they began walking towards the table where Kim and Antonio sat. 

Jay nodded in acknowledgement of what his brother was saying. He had realized he wanted more than friendship with Hailey, and if he needed to act on his feelings before it was too late.

**Notes for the Chapter:**

> I know people don’t like Upzek, but I love Adam and I love the side of Hailey we got to see when they were together. I love to use Adam and Hailey flirting to make Jay jealous! I hope you enjoyed and I hope to update in a week or 2!

**Author's Note:**

> Thank you for reading. Due do the workforce returning to the office, I will not be able to update as frequently as I would like. I am aiming for once a week so finger crossed!


End file.
